the nucleus march 2014 issue

8/13/2019 The Nucleus March 2014 Issue

1/20

http://www.nesacs.org

March 2014 Vol. XCII, No. 7

NO

E A S

T ERNSECT

IONAMER

ICAN

CHEM

ICA

L

SOCI

ETY

FOUN

DED1898

NE

S

AC

S

Monthly Meeting2013 Nobel Laureate Martin Karplus to speak at the

Boston/Cambridge Courtyard Marriott

Summer Scholar ReportBy Kyle Murphy and Edward J. Brush, Bridgewater

State University

Chem Camp fromthe Other SideBy Jacob Sanders

Norris AwardSymposium

Monday, March 17, 2014 at Omni Dallas Hotel


2/20

2 The Nucleus March 2014

This past June, I had the opportu-nity to serve as the Peer Mentor at theUS National Chemistry Olympiad(USNCO) Study Camp, held at the USAir Force Academy in ColoradoSprings. The program, colloquiallyreferred to as Chem Camp, bringstogether the top 20 high-school chem-istry students across the entire country(based on the national selection exam)to prepare them for the InternationalChemistry Olympiad.

For two weeks, the students dedi-

cate themselves to chemistry: theyattend advanced theoretical lectures onorganic, inorganic, physical, analytical,and biochemistry; they work with thementors and with each other to solvechallenging problems in all of thesefields; and they work in the laboratoryevery afternoon to master advancedtechniques. At the end, the top fourstudents, along with two alternates, areselected to represent the United Statesat the International ChemistryOlympiad, which comprises a five-

hour theoretical exam and a five-hourlaboratory practical exam.As a high school student, I

attended Chem Camp in June 2005,where I was selected to attend the 37 th

International Chemistry Olympiad inTaipei, Taiwan. The entire experience,from the study camp to the interna-tional exam, was such a formative onethat I jumped at the opportunity toreturn this year to the study camp asthe Peer Mentor. This article is my

behind-the-scenes look at Chem Camp

from the other sidethat of thementors and instructors.Preparation for the study camp

begins long before June. In January,the host country of the upcoming inter-national exam releases a book ofPreparatory Problems: about 30 theo-retical problems and 10 laboratoryexperiments. The problems are reallyflippin hard, creatively combiningmany advanced topics into a singlequestion, and they define the scope ofthe international competition by indi-

cating which topics will be empha-

sized. Since the competition this pastyear was hosted by Russia, a countrywith a long olympiad tradition, the

pro bl em s we re eve n ha rd er tha n

usualmany at the level of a graduatestudent!My first task as Peer Mentor

long before the camp startedwas towork through the theoretical problems.Some took many hours; othersrequired that I learn topics far afieldfrom my expertise (for me, the realzingers are inorganic chemistry!). Thechemistry nerd in me loved this

processI got to confront topics I had-nt thought about in a long time. Iknew it was important to understand

every problem inside-out, as I wouldsoon face 20 bright students askinghard detail-oriented questions. In addi-tion, I searched for other problemsmostly from old olympiadexamscovering similar concepts.These could be used as practice prob-lems or exam questions.

Armed with a large binder full ofmy notes and solutions to the Prepara-tory Problems, I arrived at the US AirForce Academy with the three mentorsthree days before the students. Those

three days went by in a blur: coordinat-

ing with lecturers, buying supplies,andmost importantlysetting uplaboratory stations and making sure allthe experiments were ready to go. Thementors took the lead in this enormoustask: prior to the camp, they tested allthe laboratory experiments in thePreparatory Problems and designedadditional experiments to give the stu-dents practice with the techniques

being emphas ized by the Russians .Their dedication to designing, tweak-ing, and managing so many compli-

cated experiments is the main reasonour team performs so strongly on thepractical component of the interna-tional exam. The three days of prepa-ration flew by and, before we knew it,the students started to arrive.

Meeting the students for the firsttime is an inspiring experience. Onestudent, barely after putting down hisluggage, started to ask me deep andsophisticated questions about advancedequilibrium techniquesa topic I wasscheduled to lecture later in the camp.

(I silently noted that I needed to makemy lecture harder and more advanced.)But most important is the camaraderiethat emerges when you bring 20 stu-dents obsessedwith chemistryfor thefirst timein the same place. One ofthe most memorable moments is theopening dinner, where the studentsreceive six college-level textbooksranging across all the subfields ofchemist ry. You can see the look ofChristmas-come-early in some of theireyessee the picture if you dont

believe me!

Chem Camp from the Other SideJacob Sanders is a Ph.D. Candidate in Chemical Physics and Head Teaching Fellow at Harvard University.

continued on page 4

From student (June 2005, top left) to mentor(June 2013, bottom)

Christmas in June! The students receive theirtextbooks.


3/20

The Nucleus March 2014 3

The Nucleus is published monthly, except June and August, by the Northeastern Section of the AmericanChemical Society, Inc. Forms close for advertising on the 1st of the month of the preceding issue. Textmust be received by the editor six weeks before the date of issue.

Editor: Michael P. Filosa, Ph.D., 18 Tamarack Road, Medfield, MA 02052 Email:filosam(at)verizon.net; Tel: 508-843-9070Associate Editors: Myron S. Simon, 60 Seminary Ave. apt 272, Auburndale, MA 02466,

Mindy Levine, 516-697-9688, mindy.levine(at)gmail.comBoard of Publications: James Phillips (Chair), Vivian K. Walworth, Mary MahaneyBusiness Manager: Karen Piper, 19 Mill Rd., Harvard, MA 01451, Tel: 978-456-8622Advertising Manager: Vincent J. Gale, P.O. Box 1150, Marshfield, MA 02050,

Email: Manager-vincegale(at)mboservices.net; Tel: 781-837-0424Contributing Editors: Morton Hoffman, Feature Editor; Dennis Sardella, Book ReviewsCalendar Coordinator: Xavier Herault, Email: xherault(at)netzero.net

Photographers: Morton Hoffman and James PhillipsProofreaders: Donald O. Rickter, Vivian K. Walworth, Mindy LevineWebmaster: Roy Hagen

Copyright 2014, Northeastern Section of the American Chemical Society, Inc.

The Northeastern Section of the AmericanChemical Society, Inc.

Office: Anna Singer, 12 Corcoran Road,Burlington, MA 01803(Voice or FAX) 781-272-1966.e-mail: secretary(at)nesacs.org

NESACS Homepage:

http://www.NESACS.orgOfficers 2014

ChairCatherine CostelloBoston University School of Medicine670 Albany Street, room 511Boston, MA 02118-2646Cecmsms(at)bu.eduChair-ElectKatherine L. LeePfizer200 CambridgePark Drive, t6014KCambridge, MA 02140katherine.lee(at)pfizer.com617-665-5664

Immediate Past ChairLiming Shao158 South Great RoadLincoln, MA 01773Shao(at)fas.harvard.edu781-518-0720Secretary:Michael SingerSigma-Aldrich3 Strathmore Rd, Natick, MA 01360774-290-1391, michael.singer(at)sial.comTreasurer:James Piper19 Mill Rd, Harvard, MA 01451978-456-3155, piper28(at)attglobal.net

Auditor:Anthony Rosner

ArchivistTim FrigoTrustees:

Peter C. Meltzer, Michael E. Strem, DorothyPhillipsDirectors-at-LargeDavid Harris, John Neumeyer, Mary Burgess,James Phillips, Ralph Scannell, John BurkeCouncilors Alternate Councilors

Term Ends 12/31/2014Katherine Lee C. Jaworek-LopesMichael P. Filosa Lawrence ScottDoris Lewis John PodobinskiMorton Z. Hoffman Stuart LevyPatrick Gordon Mukund ChorghadeMary Burgess Sonja Strah-PleynetTerm Ends 12/31/2015Catherine E. Costello Jerry JasinskiRuth Tanner Stephen LantosKen Mattes Norton P. Peet

Michaeline Chen Wilton VirgoJackie ONeil VACANTTerm Ends 12/31/2016Michael Singer Sophia R. SuMary Shultz Leland L. Johnson, Jr.Robert Lichter Mary MahaneyHeidi Teng Andrew ScholteMarietta Schwartz Raj Rajur

ContentsChem Camp from the Other Side__________________________2

By Jacob Sanders

Monthly Meeting_______________________________________52013 Nobel Prize Winner Martin Karplus of Harvard University to speak at theCambridge/Boston Courtyard Marriott

Martin Karplus ________________________________________5By Jack Driscoll

Announcements______________________________________7,8Nominations wanted for the Theodore William Richards Award for Excellence inTeaching Secondary School Chemistry and the James Flack Norris Award forOutstanding Achievement in the Teaching of Chemistry

Norris Award Symposium at the Dallas Meeting____________8,9NESACS Candidates for 2014 ____________________________9Summer Scholar Report________________________________10

Applying Green Chemistry Principles in the Electrophilic Bromination of Indole-3-Acetic Acid

By Kyle Murphy and Edward J. Brush, Bridgewater State University

January Meeting Report________________________________14By Xavier Herault and Jack Driscoll

ACS Northeastern Section at Fenway Park!_________________13Red Sox Game, Tuesday, May 6, 2014

March Historical Events in Chemistry_____________________15By Leopold May, Catholic University of America

Northeastern Student Research Conference________________20Cover: March Speaker and 2013 Nobel Prize Winner in Chemistry Professor

Martin Karplus shown in his office with Jack Driscoll, Public Relations Chairfor NESACS. See Page 5 for Dr. Driscoll's interview of Professor Karplus (Photocourtesy of Jack Driscoll).

Editorial Deadlines: May 2014 Issue: March 15, 2014September 2014 Issue: July 15, 2014

May 2014 Issue: March 15, 2014

Al l Ch ai rs of st an di ngCommittees, the editorof THE NUCLEUS, andthe Trustees of Section

Funds are members of theBoa rd o f Directo rs. AnyCouncilor of the American Chemical Soci-ety residing within the section area is an ex

officio member of the Board of Directors.


4/20


After the first night, the ChemCamp routine begins in earnest the fol-

lowing morning: breakfast, four hoursof lecture, lunch, four hours of labora-tory, dinner, study and relaxation timein the evening, lights out. On top ofthis standard routine, which lasts tendays, are piled three exams, one finalexam, and two lab practical exams.

As Peer Mentor, I attended all ofthe morning lectures with the students.My main goal was to help the students

bridge the gap between the theoreticallecture material and the level of hands-on problem solving expected in the

Preparatory Problems. During eachlecture break, I would announce whichPreparatory Problems the studentswere prepared to attempt and the stu-dents would come to me with ques-tions. Near the end of the camp, I alsogave three lectures focusing on analyti-cal chemistry: advanced equilibriumtechniques, advanced titrations, and amore general how-to-solve-a-problem-when-you-have-no-idea-whats-going-on lecture.

One thing that really distinguishes

Chem Campers from other students Ihave taught, including most Harvardundergraduates, is how demandingthey arein the best way possible.They never left any academic stone

unturned. If a lecturer skipped steps ina derivation, students would clusteraround the blackboard during the breakto fill in the missing steps. Similarly,many students loved taking assigned

problems and making them harder:What if you dropped a key assump-tion? Could the result be generalized?I often found that, rather than teachingthese students, I ended up interactingwith them as colleaguesparticipatingexcitedly in the give-and-take of theirdiscussions, but letting them guide the

way. I think this is the only group ofstudents I have ever had that was moretalkative inside the classroom than out-side of it.

After lunch, the students typicallyspent the full afternoon working in thelaboratory. While I occasionallyobserved the students and assistedthem with instrumentation, as a theo-rist, I ultimately left most of the labo-ratory responsibilities to thementorswho did a fantastic job

preparing the students for the practicalexam at the International ChemistryOlympiad. Instead, I used the after-noons to prepare for the evenings:researching the answers to particularlytough student questions and cullingthrough old International ChemistryOlympiad exams to satisfy the stu-dents endless thirst for more practice

problems.After dinner, in the evenings, the

students couldfinally relax. Games ofmafia proved especially popular and,

by the end of the camp, we had com-pl icated the standard rules so muchthat I was at my wits end to imple-ment them correctly. Even during thisevening relaxation, the uniquely cre-ative talents of the students shonethrough: two of them went off todevelop a mathematical model to findthe optimal number of mafia membersneeded to make the game as fair as

possible. Many of the students, even

2013 NESACS Golf Sponsors

LSNE Lyophilization Services of NE

Strem ChemicalLitman Gerson

Sage Chemical

Davos

Prime Organics

Brian OReilly, LLP, Patent Litigation

Johnson Matthey

IRIX Pharmaceuticals

Cambridge Major

OConner Carnathan and Mack, LLC

Edelstein and Co.

Chengda - Social Hour Sponsor

continued on page 16

Chem CampContinued from page 2

Stephen Ting, Saaket Agrawal, and Jessica Xuworking together at the whiteboard during abreak in lecture.


5/20


Monthly MeetingThe 939

th

Meeting of the Northeastern Section of the AmericanChemical Society

Motion: Hallmark of Life. From Marsupials to Molecules

Dr. Martin Karplus, Theodore William Richards Professor of Chemistry,Emeritus, Department of Chemistry and Chemical Biology, Harvard Uni-versity and Professeur Conventionne, Universit de Strasbourg, France,2013 Nobel Prize in Chemistry

Thursday, March 6, 2014

Courtyard Marriott Boston/Cambridge777 Memorial Drive, Cambridge, MA 02139

Agenda

4:30 Board Meeting in Great Room5:30 Social Hour in The Ballroom

6:30 Dinner in The Ballroom

7:30 Welcome, Dr. Catherine Costello, NESACS ChairIntroduction, Dr. John N. Driscoll, NESACS Public Relations ChairEvening Lecture: Dr. Martin Karplus

THE PUBLIC IS INVITED

For those would like to join us for dinner, please make a reservation by noon,Thursday, February 27 using PayPal: http://acssymposium.com/paypal.html.Select the pay with credit or debit card option and follow the additional instruc-

tions on the page. Cost: Members, $30; Non-members, $35; Retirees, $20;Students, $10.If you wish, join us for the evening program only, starting at 7:30 PM.

Please pre-register using PayPal http://acssymposium.com/paypal.html. Selectthe Seminar Only option. The fee is $1. New members or those seekingadditional information, contact the NESACS administrative secretary, AnnaSinger, at [email protected] (preferred) or (781) 272-1966, 9 AM - 6 PM.Dinner reservations not cancelled at least 24 hours in advance must be paid.

Parking:Parking in the Courtyard Boston Cambridge Marriott is free of charge for thoseattending this event.

Martin

KarplusBy Jack Driscoll,NESACS Public Relations ChairThe information for this article wastaken from an interview with Prof.Karplus in January 2014, an article thathe wrote in 2006 (Annual Review of

Biophysics 35 , 1-47, 2006) and theNobel Prize website.

Nobel Prize BackgroundThe Nobel Prize is awarded to the

person or persons who have made the

most important chemical discovery orimprovement. The Nobel Prize inChemistry for 2013 was awarded

jointly to Martin Karplus (Universitde Strasbourg, France, and HarvardUniversity), Michael Levitt (StanfordUniversity School of Medicine), andArieh Warshel (University of SouthernCalifornia) for their work on thedevelopment of multiscale models forcomplex chemical systems (http://www.nobelprize.org/).

Karplus says, If you like to know

how a machine works, you take it apartand put it together again. We do thatfor molecules.

The Nobel Prize in Chemistry hasbeen awarded to 166 Laureates sinceits inception in 1 901 (http://www.nobelprize.org/nobel_prizes/facts/chemistry/ ). The average age of all Chem-istry Laureates at the time of the awardis 58 years. Only four women havereceived the Nobel Prize in chemistry:Marie Curie (1911), Irne Joliot-Curie(1935), Dorothy Crowfoot Hodgkin

(1964), and Ada Yonath (2009). , Tenwomen have received a Nobel Prize inPhysiology or Medicine

Martin Karplus delivered hisNobel Lecture on 8 December 2013, atAula Magna, Stockholm University,where he was introduced by ProfessorSven Lidin, Chairman of the NobelCommittee for Chemistry (http://www.nobelprize.org/nobel_prizes/chemistry/laureates/2013/karplus-lecture.html) .

Some excellent background mate-rial on his life and his research was

Copyright Nobel Media AB 2013, Photo: Niklas Elmehed

continued on page 6


6/20


described by Martin Karplus in a 2006article in the Annual Review of Bio-

physics (http://www.annualreviews.org/doi/pdf/10.1146/annurev.biophys.33.110502.133350).

There are a number of videos onMartin Karplus that can be found onhttp://www.youtube.com in whichMartin talks about winning the NobelPrize: (http://www.youtube.com/watch?v=C5mpmPZGChA) . Martinexplains his work to young students(http://www.youtube.com/watch?v=Hc

N02yYerCg), and describes how hestays creative (http ://www.youtube.com/watch?v=9zM3dF5GYg0 ).

A 45-minute interview of him canbe found at http://www.nobelprize.

org/podcast/. For more information,just Google Mar tin Karplus+ Nobelprize.

A photo of the Nobel Medal is shown

in Figure 1BiographyMartin Karplus was born in Austria in1930 and the family lived there untilthe German occupation of Austria in1938. The family lived in Brightonwhen they first immigrated to the U.S.

but moved to Newton because of a bet-ter school system.

How did he get from there to here?

1. Family backgroundMartins maternal and paternal

grandfathers were both physicians. Hisfather was a mechanical engineer andhis mother worked as a nurse for herfather. His uncle invented the Variacor variable transformer which has beenused by most chemists. A friend intro-duced him to the Lowell lectures. Twoof Martins daughters are physicians.His brother Robert was an eminent the-oretical physicist and was deeplyinvolved in science education in hissecond career.

2. Early yearsMartins interest in biology was

stimulated by receiving a microscopeat an early age, by his fathers interest

in nature, by attending the Lowell lec-tures, and by his interest in birds.Martin had a supportive environ-

ment in Newton elementary and juniorhigh schools. In high school, where his

brother Robert had been an excellentstudent, the teachers presumed thatMartin would not be the student thathis brother had been. Martin had con-siderable problems interacting with thechemistry teacher in particular.

His brother suggested to him thathe take the Westinghouse Science Tal-ent Search exam. After he could notget a recommendation from his chem-istry teacher, he went to the principal,took the test, and became a Westing-house Scholar.

3. CollegeMartin attended Harvard as a

Westinghouse scholar. He wasexpected to go into medicine, but dur-ing his freshman year he felt that acareer in the sciences would be moreinteresting and productive. He wasinterested in biology but chose the

unique Chemistry and Physics Pro-gram at Harvard to give him a betterunderstandin g of biology. I amamazed that Martin, in his freshmanyear of college, was able to select thecourses and direction of his career atsuch a young age.

Martin attended graduate school atCalifornia Institute of Technology. Hestarted as a biology major but thatchanged quickly as a result of the firstseminar he gave; his advisor said thatit was the worst seminar that he ever

heard. Martin was devastated, butanother Professor told him that hesays this to everyone and that Del-

br uck pr obab ly did no t unde rs tandwhat Martin had said. In any event,Martin decided to switch to chemistryand went to work under Kirkwood.Several months later, Kirkwoodaccepted an offer from Yale and invitedhis students to join him. Prof. LinusPauling had stopped taking graduatestudents but he asked Kirkwoods stu-dents if they wanted stay at Cal Tech

Martin KarplusContinued from page 5


Figure 1.Nobel Medal
http://www.nobelprize.org/podcast/http://www.nobelprize.org/podcast/http://www.nobelprize.org/podcast/http://www.nobelprize.org/podcast/


7/20

THEODORE WILLIAM RICHARDS AWARD

FOR

EXCELLENCE IN TEACHING

SECONDARY SCHOOL CHEMISTRY

January 2014

Do you know an excellent Chemistry Teacher to nominate for the 2014 Theodore William RichardsAward for Excellence in Teaching Secondary School Chemistry sponsored by the Northeastern Sectionof the American Chemical Society? We feel that there are many outstanding and exceptional Chemistryteachers in the Northeastern Section, so please take the time to nominate one of the deserving faculty mem-

bers from your school.

The prestigious Theodore William Richards Award for Excellence in Teaching Secondary SchoolChemistry is presented annually to a teacher who demonstrates exceptional innovation and dedication ininspiring students, communication in the principles of chemistry in and out of the classroom, and leader-ship in influencing and mentoring other chemistry teachers. Sound like someone you know or work with?Then use the nomination form at http://www.nesacs.org to recognize that teachers talents.

Nominations by STUDENTS (current or former), COLLEAGUES, DEPARTMENT HEADS, or INDI-VIDUALS who choose to self-nominate are eligible for consideration. The deserving recipient will be hon-ored at the Education Night ceremony in May and presented with a $1,500 cash prize and Certificate ofRecognition.

Thank you for your attention in bringing recognition to the talented Chemistry Teachers of the Northeast-ern Section, and hopefully the next deserving recipient of the prestigious Theodore William RichardsAward will be from your school.

Please send nomination forms by April 11, 2014 to:

Richards Award CommitteeAttn: Steve LantosBrookline High School115 Greenough StreetBrookline, MA 02445Email: [email protected]

Thank you,Richards Award Committee


ADMINISTRATIVE SECRETARY

12 CORCORAN ROADBURLINGTON, MA 01803

Telephone: 781-272-1966

E-Mail: [email protected]

NORTHEASTERN SECTION

AMERICAN CHEMICAL SOCIETY


8/20

Norris

AwardSymposiumat DallasMeetingIt may seem hard for some of us toimagine, but 2014 will see the award-ing of the 50 th James Flack NorrisAward in Physical Organic Chemistry.This occasion is being marked with asymposium on Monday, Mar. 17, at theAmerican Chemical Society (ACS)spring national meeting in Dallas. Thesymposium was organized by E.Thomas Strom and Jeffrey I. Seemanof the ACS Division of the History ofChemistry with the Northeastern ACSSection and the ACS Division ofOrganic Chemistry as co-sponsors.The symposium is titled Fifty Yearsof the James Flack Norris Award. TheFoundations of Physical OrganicChemistry.

The opening comments will begiven by Section Chair Catherine

Costello. The introductory talk will begiven by section member ArthurGreenberg of the University of NewHampshire. His title is James Flack

Norris, A Pioneer in Chemical Educa-tion and His Early Contributions inPhysical Organic Chemistry. This talkwill reveal some previously unknownmaterial on Norris. The symposiumwill also include seven talks by earlywinners of this award. Those speakersare Edward Arnett, Ronald Breslow,Andrew Streitwieser, Jr., John Brau-man, Paul Schleyer, Kendall Houk,and Michael Wasielewski.

The symposium will concludewith a panel discussion from additionalwinners of the award: Matthew Platz(the 2013 winner), John Baldwin, NedPorter, Hans Reich, John Roberts, andMichael Wasielewski again. The sym-

posium will be held at the Omni DallasHotel.

This symposium honors one ofthis sections most distinguished mem-

bers, James Flack Norris, and also thisimportant award, which has kept Nor-ris memory green. We hope that thosesection members attending the springACS meeting will be present to heartalks from these great physical organicchemists.


Call for

NominationsThe 2014 James Flack NorrisAward for OutstandingAchievement in the Teachingof Chemistry

Deadline: April 15, 2014

Nominations are invited for the 2014James Flack Norris Award, which con-sists of a certificate and an honorariumof $3,000 and is given annually by the

Northeastern Section (NESACS). Thepresentation will take place at a cere-mony and dinner in November 2014,and will include a formal address bythe awardee. The Award was estab-lished in 1950 by NESACS to honorthe memory of James Flack Norris(1871-1940), a professor of chemistryat Simmons College and M.I.T., chairof NESACS in 1904, and ACS Presi-dent in 1925-26.

No mi ne es sh ou ld hav e se rvedwith special distinction as teachers ofchemistry at any level: secondaryschool, college, and/or graduateschool. With the presentation of thefirst Award in 1951, awardees haveincluded many eminent teachers at alllevels whose efforts have had a wide-ranging effect on chemical education.The recipient will be selected from aninternational list of nominees whohave served with special distinction asteachers of chemistry with significantachievements.

A nomination in the form of a let-ter should focus on the candidatescontributions to and effectiveness in

teaching chemistry. The nomineescurriculum vitae should be includedand, where appropriate, a list of hon-ors, awards, and publications related tochemical education. Seconding lettersmay also be included; these shouldshow the impact of the nom ineesteaching for inspiring colleagues andstudents toward an active life in thechemical sciences, and attest to theinfluence of the nominees other activi-ties in chemical education, such astextbooks, journal articles, or other

pr ofe ss io nal ac ti vit y at th e lo ca l,national, and international level.

The nomination materials shouldconsist of the primary nomination let-ter, supporting letters, and the candi-dates curriculum vitae. Reprints orother publications should NOT beincluded. The material should notexceed thirty (30) pages, and should be

submitted electronically in Adobe PDFformat through April 15, 2014 to Ms.Anna Singer, NESACS AdministrativeSecretary .For more information about the Award,see .

Questions about the Award or thenomination process should be directedto the Chair of the Norris Award Com-mittee, Professor Doris Lewis,.

New MembersInvitation to attend a meeting

You are cordially invited to attend oneof our upcoming Section meetings as aguest of the Section at the social hourand dinner preceding the meeting.

Reservations for new membersand for additional information, contactthe secretary Anna Singer at (781)272-1966 between 9am and 6pm or e-mailat [email protected]

Q. Exactly, how many awards and

scholarships does NESACS sponsor?

A) One b) Two c) Many

www.nesacs.org/awards
http://www.nesacs.org/awards_main.htmlhttp://www.nesacs.org/awards_main.html


9/20

Fifty Years Of

The James FlackNorris Award

MONDAY, MAR. 17, 2014

OMNI DALLAS HOTEL

8:55-9:00 a.m. Opening Remarks, Catherine Costello, Northeast-ern ACS Section

9:00-9:30 a.m. Arthur Greenberg, University of New Hampshire,James Flack Norris, A Pioneer in Chemical Edu-cation and His Early Contributions in PhysicalOrganic Chemistry

9:30-10:00 a.m. Edward M. Arnett, Duke, Some ThermochemicalStudies in the 1960s and 70s

10:00-10:30 a.m. Ronald Breslow, Columbia, Aromaticity and Con-ductivity in Molecular Wires

10:30-10:45 a.m. Break

10:45-11:15 a.m. Andrew Streitwieser, Jr., UC-Berkeley, Hydrogen

Isotopes in Physical Organic Chemistry

11:15-11:45 a.m. John I. Brauman, Stanford, Adventures in Physi-cal Organic Chemistry

11:45 a.m.-1:55 p.m. Lunch Break

1:55-2:00 p.m. Opening Remarks, Jeff Seeman, Moderator

2:00-2:30 p.m. Paul Schleyer, Georgia, Norbornyl Cations StillFascinate

2:30-3:00 p.m. Kendall N. Houk, UCLA, Physical Organic Chem-istry with Computations: Pericyclic Reactions

3:00-3:15 p.m. Break

3:15-3:45 p.m. Michael Wasielewski, Northwestern, Understand-ing Electron Transfer Reactions: A Case Study inPhysical Organic Chemistry

3:45-4:45 p.m. Panel Discussion, Whither Physical OrganicChemistry?Panelists: John Baldwin, Matthew Platz, NedPorter, Hans Reich, John Roberts, MichaelWasielewski


NESACS

Candidatesfor 2014Chair

Jerry P. JasinskiWilton Virgo

SecretaryMichael Singer

TreasurerJames U. Piper

TrusteeJack Driscoll

Ruth TannerAuditor

Anthony L. RosnerCouncilor/Alternate Councilor

Mary BurgessMukund S. ChorghadeMorton Z. HoffmanPatricia A. MabroukMichael FilosaPatrick GordonLiming ShaoChristine Jaworek-LopesDoris I. Lewis

Chris MoretonJohn PodobinskiMary Jane ShultzSonja Strah-PlaynetAnna Waclawa SromekMark TebbeRalph T. ScannellAndrew Scholte

Director-at-LargeRalph T. ScannellJohn BurkeAndrew Scholte

Nominating Committee

Mukund S. ChorghadeAnna Waclawa SromekJohn Williams

Norris AwardMary A. MahaneyMark TebbeChris MoretonRobert Goodnow

Petition Candidates: Any group com-prising 2 per cent or more of the North-

eastern Section (136 members) may

nominate candidates See NESACS

website for details.


10/20


Introduction

The goals of green chemistry are to reduce or eliminate theuse of hazardous reagents, prevent the synthesis of toxic

products and byproducts, and improve the overall efficiencyof chemical reactions. Green chemistry is incredibly impor-tant today as chemical products are produced and usedaround the world, resulting in the use and generation of haz-ardous chemicals, and unintended consequences to humanhealth and the environment. Paul Anastas and John Warnerdeveloped the 12 Principles of Green Chemistry1, Figure 1,to provide the framework for a sustainable future in the

design of more efficient technologies to produce consumerproducts that are better, safer and cheaper.

3-Bromooxindole-3-acetic acid (BOAA) is an impor-tant intermediate in our groups work on the synthesis ofsmall-molecule mechanism-based enzyme inhibitors.

BOAA is readily transformed into a variety of oxindole

derivatives designed to inhibit specific enzymes known tobe therapeutic targets, Figure 2.

The traditional method to synthesize BOAA fromindole-3-acetic acid (IAA) is illustrated in Figure 3.2N-bro-mosuccinimide (NBS) serves as brominating agent, and tert-

butanol is both solvent and reactant, p roviding the C-2oxindole oxygen. We have found major complications withthis synthesis, including the use and generation of hazardouschemicals, poor atom economy (30%), and low percentyield (25%). NBS is a major source of the waste byproductsincluding HBr and succinimide (see box in Figure 3). Notethat of the 24 atoms in two mole equivalents of NBS, onlyone bromine atom is incorporated in the final BOAA prod-uct, contributing to the low atom economy. Based on litera-ture precedent,3,4 we suspected that the low percent yieldwas primarily due to poor regioselectivity in the bromina-tion of IAA, resulting in the formation of isomeric bromi-nated products.

Summer Scholar ReportApplying Green Chemistry Principles in the Electrophilic Bromination of Indole-3-Acetic Acid

Kyle Murphy and Edward J. Brush, Department of Chemical Sciences, Bridgewater State University, Bridgewater, MA

Figure 1. The Twelve Principles of Green

Figure 2.Potential mechanism-based inhibitors based onoxindole derivatives.

Figure 3. Traditional method to synthesize BOAA from IAA.


11/20

The goal of this research project was to obtain a betterunderstanding of the overall BOAA synthetic process, andapply the Principles of Green Chemistry to improve reactionefficiency. Utilizing 1H NMR we have: identified four major

products from IAA bromination, determined that the reac-tion process occurs in two discrete steps, and obtained keymechanistic insight that is helping us improve on the overallefficiency of this reaction.

ExperimentalAll reagents were purchased from Sigma-Aldrich or FisherScientific and used without further purification. Tert-butanolwas stored over 3 molecular sieves. Nuclear MagneticResonance (NMR) spectra were obtained on a JEOL ECX-400 MHz instrument.

Evaluating different reaction parameters for the synthe-sis of BOAA would require substantial amounts of solventand reagents, produce liters of hazardous waste, and anentire day would be needed to run and analyze a single reac-tion. To optimize our green chemistry approach, wedeveloped a quick, reproducible and efficient reactionscreening method that required milliliters of solvent, mil-ligrams of reagents, and minimized waste. The screeningmethod used quantitative NMR (qNMR)5 to determine %yield and recovery. In qNMR the quantity of a particularanalyte could be determined by comparing the integratedvalue of an analyte signal of known number of Hs to theintegrated value of the vinyl protons (2H, 6.33 ppm) of the

maleic acid internal NMR reference standard.6

The standard screening reaction used 200 L of a 0.174M solution of IAA in tert-butanol (6.11 mg, 34.9 mole)added to a 10 mL reaction vial with an additional 800 L oftert-butanol. The solution was stirred at room temperatureand reaction initiated by the addition of two mole equiva-lents (12.4 mg, 69.8 mole) of NBS. After stirring for anadditional 10 minutes, the reaction was worked up by evap-oration of tert-butanol solvent on a high vac, and then sus-

pending the residue in diethy l ethe r. The succ in imidebyproduct was removed by pipette filtration into a 10 mLround bottom flask and solvent again evaporated underreduced pressure. Acetone-d6 containing 0.05% TMS (1.0

mL) was added to dissolve the residue, then 2.00 mg(0.0172 mol) of maleic acid dissolved in 25 L of dimethyl-sulfoxide-d6 was added as the internal qNMR referencestandard. This screening method allowed us to run and ana-lyze up to five reactions per day. This general procedureallowed us to test the effect of various reaction parameterson the product distribution, including the IAA:NBS stoi-chiometry, and addition of potential catalysts.

Results and DiscussionThe traditional reaction mixture with two equivalents of

NBS was worked up to remove residual solvent and succin-imide byproduct, and the residue analyzed by 1H NMR, Fig-ure 4. By focusing exclusively on signals in the aromatic

region, we were able to identify four major products fromIAA bromination, Figure 5.

We propose that the bromination of IAA with twoequivalents of NBS occurs in two reaction steps as shown inFigure 6. In Reaction #1 the initial equivalent of elec-trophilic bromine adds rapidly (within seconds) to the C-2,3double bond (possibly with assistance from N-1), followed

by addition of tert-butanol to C-2. Subsequent eliminationsteps (mechanism not shown) produce oxindole-3-aceticacid (OAA). We also observe 5-bromo-OAA most likelyfrom the addition of a second equivalent of bromine to C-5of OAA (consistent with literature precedent7). Reaction #2

is slow addition of the second equivalent of NBS to C-3,producing BOAA and 5-bromo-BOAA. Our proposal isconsistent with the observation of C-3 and C-5 brominated

products from indoles.3,4,7 The C-3 position of indoles isknown to undergo bromination very rapidly, while C-5

bromination was based on the known activating effects ofthe N-1 nitrogen (C-7 brominated product was notobserved). The authors from these original studies employedindirect methods for product analysis based on chemicaltransformation to known compounds, followed by melting

point determination. Our work is the first to conclusivelyidentify the IAA bromination products using 1H NMRanalysis.


Figure 4. 1H NMR (400 MHz) of IAA reaction with twoequivalents of NBS.

Figure 5. Oxindole byproducts of complete IAA-NBS reac-tion: (a) 3,5-dibromooxindole-3-acetic acid (5-Bromo-

BOAA), (b) 3-bromooxindole-3-acetic acid (BOAA), (c)5-bromooxindole-3-acetic acid(5-Bromo-OAA), (d) oxin-

dole-3-acetic acid (OAA).


Summer ScholarContinued from page 10


12/20

To test this idea we ran the traditional BOAA synthesis fromIAA by adding NBS in two separate steps. The results ofthese reactions (data not shown) clearly show that additionof one mole equivalent of NBS produces OAA and 5-

bromo-OAA. Subsequent addition of a second NBS equiva-lent gives the typical product distribution shown in Figure 5.

As our preliminary data suggested that addition of thefirst equivalent of electrophilic bromine to IAA was the crit-ical step, in that multiple oxindole byproducts are producedand that this poor regioselectivity was ultimately responsiblefor the poor efficiency of this reaction. As we could nowsuccessfully run the BOAA synthesis as two separate reac-tions (Figure 6), this allowed us to focus exclusively onReaction #1, and conduct preliminary experiments toimprove the poor regioselectivity.

It has been reported that the selectivity of NBS-medi-ated brominations can be controlled with amides andamidines that act as Lewis base catalysts by either facilitat-ing the regioselective transfer of bromine from NBS to theacceptor, or stabilizing the bromonium ion intermediate.8-11

Furthermore, in the traditional synthesis we suspected thatHBr generated during the course of Reaction #1 catalyzesC-3 halogenation of OAA through an enol intermediate. Wesubsequently surveyed a variety of Lewis base, and acid cat-alysts for improving the overall efficiency of BOAA synthe-sis. Representative data are presented in Table I.

When dimethylformamide (DMF) was added to Reac-tion #1 there was modest improvement in the regioselectiv-

ity by promoting BOAA production as compared to theoxindole byproducts. Similar results were obtained whenacetic acid was added to Reaction #2, consistent with acidcatalyzed halogenation. Furthermore, addition of triethy-lamine inhibited production of BOAA as well as other oxin-dole byproducts, possibly by neutralizing any HBr producedin Reaction #1.

Conclusions and Future WorkWe have applied Green Chemistry principles and NMRanalysis to better understand the synthetic reactions in the

preparation of BOAA from IAA. We have identified fouroxindole products from this reaction, and determined that

IAA bromination occurs in two discrete steps. These prelim-

inary results have provided key mechanistic insight that willhelp us improve the low yield and overall efficiency of thisreaction. We are currently evaluating additional Lewis basecatalysts to improve the regioselectivity in Reaction #1, andthe effect of acid catalysts for Reaction #2. We are also veryinterested in developing an efficient gram-scale synthesis ofoxindole-3-acetic acid (OAA) in Reaction #1, as this com-

pound has recently been identified in the regulation of auxinhomeostasis and response mechanisms in plants.12

AcknowledgementsThis research was supported by a 2013 Norris-RichardsSummer Scholarship awarded by NESACS, and a Bridge-water State University Center for Sustainability summer

2012 grant. The author would like to thank his researchmentor Dr. Edward Brush, and Dr. Steven Waratuke for hisAdvanced NMR class. The JEOL ECX-400 MHz NMR wasobtained through NSF-MRI grant 0421081.

References1Anastas, P. T.; Warner, J. C. Green chemistry: theory and

practice; Oxford University Press: Oxford [England]; NewYork, 1998.2Hinman, R.L and Bauman, C.P. (1964), Reactions of N-Bromosuccinimide and Indoles. A simple synthesis of 3-

bromooxindoles,J. Org. Chem. 29, 1206-1215.3Lawson, W.B., Patchornik, A., and Witkop, B. (1960),

Substitution, oxidation and group participation in thebromination of indoles,J. Amer. Chem. Soc., 82: 5918-23.4Condie, G.C., Channon, M.F., Ivory, A.J., Kumar, N. andBlack, D.St.C. (2005), Regioselective reactivity of some5,7-dimethoxyindoles,Tetrahedron, 61(21): 4989-5004.5Peterson, J. (1992), 1H NMR Analysis of Mixtures UsingInternal Standards,J. Chem. Educ., 69 (10): 843-5.6JEOL Resonance Application Note NM090009E (2011),What is qNMR (quantitative NMR)? www.jeol.co.jp(accessed October 2013).7Sumpter, W.C., Miller, M., and Hendrick, L.N. (1945), Astudy of certain brominated derivatives of oxindole,J.

Amer. Chem. Soc., 67(10): 1656-8.




Figure 6. Proposed reaction scheme for IAA bromination. Table I. %Composition of oxindole products as a functionof reaction conditions


13/20


8Denmark, S.E. and Burk, M.T. (2010),

Lewis base catalysis of bromo- andiodolactonization, and cycloetherifica-tion, Proc . Na tl. Ac ad . Sc i. US A,107(48), 20655-20660.9Pathak, T. P. and Miller, S. J. (2012),Site-selective bromination of van-comycin,J. Amer. Chem. Soc., 134,6120-6123.10Ahmad, S. M., Braddock, D. C.,Cansell, G., Hermitage, S. A., Red-mond, J. M., and White, A. J. P.(2007), Amidines as potent nucle-ophilic organocatalysts for the transfer

of electrophilic bromine from N-bro-mosuccinimide to alkenes, Tetrahe-dron Letters, 48, 5948-5952.11Ahmad, S. M., Braddock, D. C.,Cansell, G. and Hermitage, S. A.(2007), Dimethylformamide,dimethylacetamide and tetramethyl-guanidine as nucleophilic organocata-lysts for the transfer of electrophilic

bromine from N-bromosuccinimide toalkenes, Tetrahedron Letters, 48, 915-918.12Pencik, A., Simonovik, B., Petersson,

S.V., Henykova, E., Simon, S., Green-ham, K., Zhang, Y., Kowalczyk, M.,Estelle, M., Zazimalova, E., Novak,O., Sandberg, G., and Ljung, K.(2013), Regulation of auxin home-ostasis and gradients inArabidopsisroots through the formation of theindole-3-acetic acid catabolite 2-oxin-dole-3-acetic acid,Plant Cell, Octo-

ber 25 Epu b ah ea d of pri nt ,http://www.plantcell.org/content/early/2013/10/23/tpc.113.114421.full.pdf(checked November 2013).


Join

NESACS

on facebook

www.facebook.com/nesacs

ACS Northeastern Section

at Fenway Park!Red Sox Game Tuesday, May 6Northeastern Section members are encouraged to bring their families, friends,and colleagues to this NESACS traditional outing. We are hoping again this yearfor pleasant weather, good company, and a winning team.

On Tuesday, May 6th we have right field box seats for the Red Sox - Cincin-nati Reds game. Our tickets reflect the lowest possible cost under the new RedSox ticket pricing policy; $45 includes handling charges and a small donation tothe Northeastern Section. Reserve your seats by mailing your check (payable to

NESACS) to Anna Singer, 12 Corcoran Road, Burlington, MA 01803. Questionsmay be sent to [email protected].

Fenway park photo from Boston.redsox.mlb.com
http://www.plantcell.org/content/early/2013/10/23/tpc.113.114421.full.pdfhttp://www.plantcell.org/content/early/2013/10/23/tpc.113.114421.full.pdfhttp://www.plantcell.org/content/early/2013/10/23/tpc.113.114421.full.pdf


14/20


January

MeetingReportBy Xavier Herault (with additionalcontent and photos provided byJack Driscoll)

The 937th Meeting of the NortheasternSection of the American Society washeld at the Holiday Inn in Brookline onThursday, January 16, 2014. Thespeakers were Dr. Heidi Erlacher, a

partner at the law firm Mintz Levin,

Cohn, Ferris, Glovsky and Popeo, P.C.Christopher Montean, a tax accountantat Ernst & Young and Dr. EddineSaiah, the Head of Chemistry at AtlasVenture, a venture capital firm. Dr.Monica Palme, a Sr. Director of DrugDevelopment at Pfizer who was slatedto speak, unfortunately, could notmake it.

The subject of the symposium wasAlternate Careers for Chemists, orWhat Do I Want to Be When I GrowUp? NESACS Chair, Cathy Costello

opened the meeting and ProgramChair, Katherine Lee was the modera-tor.

The three speakers first describedwhen and how they knew it was timefor them to move their careers into anew direction after practicing chem-istry. Each has taken a different route.For Dr. Heidi Erlacher, it was duringher doctoral work at the MassachusettsInstitute of Technology. For Christo-

pher Montean, it was while a few yearsinto his chemistry career at Corning.

For Dr. Eddine Saiah, it was after atwenty-year career in medicinal chem-istry that saw him reach the position ofDirector of Chemistry at Pfizer inCambridge. However, the commontheme for all was the realization that alife in the lab or in meetings was notfor them anymore and that their otherinterests (law, finance or starting new

biotech companies) were stronger.Each speaker offered words of

advice to other chemists consideringmaking a change. You never know

who you can meet in your everyday

life who will open your mind to newopportunities (Dr. Heidi Erlacher).Sometimes it can be a big change butyou need to learn to be comfortable

be in g in an un comf or ta ble ti me ofchange (Christopher Montean). At theend, you dont choose a job, the jobchooses you (Dr. Eddine Saiah).

A transition to a career in the lawcould be either going to law schoolright after the doctorate, or starting in alaw firm as a technical advisor and

going to law school part-time in theevening. A change to a career infinance would require going back toschool to pursue a Masters in account-ing and maybe even a concurrentMBA. A jump to business and being aventure capitalist would require cash-ing in during a very successful scien-tific career.

After the panelists described theirsituations, the floor was opened to theaudience. The questions continued fornearly an hour before the meeting was

closed.NESACS PR Chair, Jack Driscolltalked for a few minutes about theACS Entrepreneurial Forum whichwill be held on April 9, 2014. A videoabout this forum can be found onYouTube: (http://youtu.be/jmSiy-cZpCnY)

NESACS thanks the speakers forsharing their unique insights into tran-sitioning into alternate careers.

Sixty-five registered for the meet-ing. Please remember you must regis-ter one week before a meeting whether

or not you intend to have dinner.After dinner an additional 50 stu-

dents arrived to attend the symposiumand take advantage of the NESACS

policy that the evening program is freeand open to the public. This meetingwas an excellent start for our new pro-gram chair, 2014 Chair-elect, Kather-ine Lee.

NESACS Chair-Elect and Program Chair,Katherine Lee Moderating the Panel on alterna-tive careers for chemists. Pictured (L-R) are

Katherine Lee, Heidi Erlacher, ChristopherMontean and Eddine Saiah.

NESACS Chair Cathy Costello opening the937th NESACS Monthly Meeting

Whats Yours?

DMPK Scientist,

LC/MS Product Specialist,

Mass Spec Operator,

Staff Investigator,

Process Chemist,

QA Manager,

Synthetic Chemist,

Lab Instructor . . .

Many local employers post positions

on the NESACS job board.

Find yours atwww.nesacs.org/jobs
http://www.nesacs.org/careers.htmlhttp://www.nesacs.org/careers.htmlhttp://www.nesacs.org/careers.html


15/20

March

HistoricalEvents inChemistryBy Leopold May, Catholic Univer-sity of America

March 1b. 1910 Archer J . P. Martin, NobelPrize (1952) with Richard L. M.Synge for their invention of partitionchromatography.

March 3b. 1918 Arthur Kornberg, researcheron the synthetic pathways by whichnucleic acids are produced; NobelPrize in Medicine (1959) withSevero Ochoa for their discovery ofthe mechanisms in the biologicalsynthesis of ribonucleic acid anddeoxyribonucleic acid.

March 8b. 1879 Otto Hahn, discovered pro-tactinium (Pa, 91) with L. Meitner;

researcher on nuclear fission with F.Strassman (1938); Nobel Prize(1944) the discovery of fission ofheavy nuclei.

b. 1886 Edward C. Kendall isolatedthyroxine, 1915; Nobel Prize inMedicine (1950) with Philip Hench& Tadeus Reichstein for their dis-coveries relating to the hormones ofthe adrenal cortex, their structure and

biological effects.

March 9b. 19 23 Wal te r Ko hn , devel ope ddensity-functional theory, whichmakes it possible to study very largemolecules; Nobel Prize (1998) withJohn A. Pople for his development ofthe density-functional theory

March 14b. 1854 Paul Ehrlich, researcher inimmunity & chemotherapy; discov-ered Salvarsan (No. 606) & neosal-varsan; improved laboratory stainingmethods; Nobel Prize in Medicine(1908) with Ilya Ilyich Mechnikov in

recognition of their work on immu-

nity.

b. 1879 Albert Einstein, researcheron photochemical effect & theory ofrelativity; Nobel Prize Physics

(1921) for his services to TheoreticalPhysics, and especially for his dis-covery of the law of the photoelec-tric effect.

March 19b. 1883 Walter N. Haworth, synthe-sized ascorbic acid (Vitamin C),1933; researcher on sugars & dextranas blood plasma substitute; NobelPrize (1937) for vitamin synthesis,with Paul Karrer.

b. 1900 Fr ederi c J. Joliot (Jol iot-Curie), Nobel Prize, (1935) withwife Irene Joliot-Curie, for produc-tion of artificial radioisotopes, in1934; proved experimentally thatneutron emission occurs in nuclearfission with H. Halban & L. W.Kowarski.

b. 1943 Mario Molino, researcher inair pollution, particularly formation& destruction of ozone; Nobel Prize(1995) with Paul Crutzen & F. Sher-wood Rowland for their work inatmospheric chemistry, particularly

concerning the formation anddecomposition of ozone.

March 21b. 1932 Walter Gilbert, researcher onthe determin-ation of deoxyribonu-cleic acid (DNA) base sequence;

Nobel Prize (1980) with Paul Berg &Frederick Sanger for their contribu-tions concerning the determinationof base sequences in nucleic acids.

March 22b. 1868 Robert A. Millikan measuredthe charge/mass ratio of the electron;

Nobel Prize in Physics (1923) forhis work on the elementary charge ofelectricity and on the photoelectriceffect.

March 23b. 1881 Hermann Staudinger, re -searcher on the chemistry of macro-molecular substances; Nobel Prize(1953) for his discoveries in the fieldof macromolecular chemistry

March 24b. 190 3 Ad olf F. J. Bute nan dt ,

researcher on sex hormones; offered

Nobel Prize (1939), for his work onsex hormones; declined on account of

Nazi decree against foreign awards.

b. 1884 Peter Joseph William Debye,

researcher in dipole moments andpowder method of x-ray diffraction;Nobel Prize (1936) for his contribu-tions to our knowl-edge of molecularstructure through his investigationson dipole moments and on the dif-fraction of X-rays and electrons ingases.

b. 1917 John Kendrew, research onstructure of hemoproteins with x-rays; Nobel Prize (1962) with MaxFerdinand Perutz for their studies ofthe structures of globular proteins

March 26b. 1911 Bernard Katz, Nobel Prize inMedicine or Physiology (1970) withJ. Axelrod and U. Von Euler for dis-coveries concerning humoral trans-mittors in the nerve terminals and themechanism for their storage, releaseand inactivation.

b. 1916 Christian Anfinsen, receivedthe Nobel prize (1972) with Stand-ford Moore and William Moore, forstudies on the relationship of struc-

tural properties of proteins and bio-logical functions, particularlyribonuclease.

March 27b. 1845 Wilhelm K. Ro ntgen discov-ered X-rays, 1895; Nobel Prize inPhysics (1901) in recognition of theextra-ordinary services he has ren-dered by the discovery of the remark-able rays subse-quently named afterhim; researcher in specific heats &heat conduction in crystals.

b. 1847 Otto Wallach, researcher on

essential oils & terpenes; NobelPrize (1910) in recognition of hisservices to organic chemistry and thechemical industry by his pioneerwork in the field of alicyclic com-

pounds. 1847-1931

March 31b. 18 90 W. La wr en ce Brag g,researcher in X-ray & crystal struc-ture; Nobel Prize in Physics (1915)with father, William H. Bragg fortheir services in the analyses of crys-tal structures by means of X-ray.



16/20


while relaxing, were still chewingaway on a tricky problemand some-times this would erupt without warninginto a full discussion. I think theseunplanned momentswith the linecompletely blurred between chemistryand hanging outwere the highlightof the camp. Where else but ChemCamp, after all, could this line be so

blurred? For me, at least, this perma-nently blurry line between chemistryand camaraderie is the defining aspectof Chem Camp.

Lights out marked the end of ajam-packed day for the students. Butfor the mentors and me, lights out wasa new beginning. With lectures to pre-

pare, laboratory write-ups to finalize,practice problems to find, and examsto write and grade, all of us had morethan enough work to keep us burningthe midnight oil long past midnight.With exams ranging from thirty to fifty

pages, and involving some of the hard-est and most creative chemistry prob-lems, perhaps the only thing harderthan taking the exams is writingthem.Even with generous help from the AirForce Academy faculty in their areasof expertise, I think it would be fair tosay that the mentors all felt a sense of

pri de (a nd exh aust io n! ) af te r ea chexamonly to start all over again thenext day. The first thing I did when Ireturned home after Chem Camp wasto go to sleepuninterruptedfor along time.

The last few days of the camprushed by in a sleepless haze: an outingto the beautiful Garden of the Gods

park, an elaborate closing banquet at

which the top six students areannounced, emotional good-byes(though many of the students will bereunited in a few short months at uni-versity), a few more days spent train-ing and testing the top six students, andultimately the selection of the finalfour students on the traveling team.

But the work of the students andmentors did not end with the camp.After returning home and sleeping offall of the end-of-camp excitement, thefour students worked together for a

month before the international compe-tition to make sure they were all well

prepared. As Peer Mentor, I helped thestudents by preparing a repository of

practice problems. Just like during thecamp, I was amazed by how endlesswas their desire for more problems.We also created a Facebook groupwhere the students could shareresources and advice. What impressed

me most was how dedicated our fourstudents were at stamping out theirweaknessesnot just individually butcollectively. With some studentsexperts on synthetic chemistry, andothers experts on mathematical chem-istry, I was blown away by the vigorwith which each side helped the otherachieve mastery. I merely helped toanswer questions and make sure theirefforts were well-directed.

Given this wonderful synergywhich developed among our students, I

am pleasedbut not surprisedtoreport that our team put in an outstand-ing performance in Moscow at theinternational competition, with DavidLiang and Runpeng Liu receiving goldmedals, and Stephen Ting and SaaketAgrawal receiving silver medals.

As for me, I am already countingdown the days until Chem Camp 2014!

Chem CampContinued from page 4

Chemistry and camaraderie all blurred into one.

Your one-stop source to career-related

links in the Chemical Sciences

WWW.NESACS.ORG/CAREERS
http://www.nesacs.org/careers.htmlhttp://www.nesacs.org/careers.html


17/20


and work with him. Martin was theonly one who chose that path. It wascertainly a wise choice for Martinsdevelopment as a theoretical chemist.

Martin was only 23 when hereceived his PhD and was headed for atwo-year postdoc sponsored by the

National Science Foundation (NSF) atOxford. He was there to find areaswhere theory could make a contribu-tion of general utility to chemistry. Hedid not want to do research that was

just of interest to theoretical chemists.By listening to lectures, talking to sci-entists, he realized that nuclear mag-netic resonance (NMR) was a vitalnew area that was in its infancy, andthat it was a field where theory couldmake a significant contribution.

4. Academic CareerHe wanted to work at a University

that had an active experimental pro-gram in NMR. The University of Illi-nois was the obvious choice. He wasoffered an instructorship in 1955 andspent the next 5 years there. Hisresearch focused on theoretical meth-

ods for relating nuclear and electronspin magnetic resonance parameters tothe electronic structure of molecules.

In 1960, he moved to Columbiawhere his focus changed to reactionkinetics. He worked in the Watson Sci-entific Lab at Columbia. He also hadan adjunct associate professorship inthe Chemistry Department at Colum-

bia. A fast computer is one of the needsof a theoretical chemist and the Watsonlab had an IBM 650 computer, whichMartin put to good use.

He continued to work on NMRand ESR, and with that computer, stud-ied the reaction of H +H2 = H2 + H,which involves exchange of hydrogenatom with H2, by calculating classicaltrajectories. His paper on H + H2 wascited by George Schatz as one of thekey papers in theoretical chemistry ofthe 20th Century.

In 1966, Karplus moved to Har-vard as a Professor and in 1979, he

became the Theodore Richards Profes-sor of Chemistry. Theodore Richards

was the first American to receive the

Nobel Prize in Chemistry in 1914.After a short time at Harvard,

Martin decided to return to his long-standing interest in biology. Arieh

Warshel (co-Nobel Laureate) joinedhis group at Harvard for a short time,and they worked on the retinal chro-mophore. Subsequently, he appliedmolecular dynamics methods to hemo-globin and protein folding.

Over a number of years, the soft-ware designated Chemistry at HAR-vardMacromolecularMechanics(CHARMM) was developed. In 1977it was first applied to a biomolecule(Figure 1) in {J.A. McCammon, B.R.Gelin, and M. Karplus, Dynamics ofFolded Proteins, Nature 267, 585-590(1977)}. This study has served toopen a new field that is now the focusof the research of an ever growingnumber of scientists.

The molecular dynamics simula-tion method, which continues to bedeveloped in the CHARMM program

by the Karplus group and many of hisformer students, as well as the largenumber of researchers effectivelyusing it for biomolecules provided the

basis for the 2013 Nobel prize. It isamazing that it took so long to awardthe Nobel prize for such an outstandingachievement.

Martin received grants from anumber of government agencies,

including NSF, NIH, AEC, and DOE,to fund his research. He only receiveda small amount of funding from onedrug company, because he did rela-

tively little applied research.Martin describes himself as a The-oretical Chemist. He goes to workevery day with his wife Marci, his lab-oratory manager, and still enjoys work-ing with his students at age 83. The

photo shows Martin enjoying tea withhis students. I enjoyed the interviewwith Prof. Karplus. I thought he wasvery insightful, friendly, and generouswith his time.

It is interesting to note that noneof the 2013 Nobel Laureates in chem-istry were born in the U.S. MartinKarplus was born in Austria, AriehWarshiel was born in Israel, andMichael Levitt was born in SouthAfrica.

Martin KarplusContinued from page 6

Figure 2. 1st Simulation of a Biomolecule using CHARMM (from Nobel Lecture)

Figure 3.Professor Karplus enjoying tea withhis students


18/20


B U S I N E S S D I R E C T O R Y

SERVICESSERVICESSERVICES


19/20


CAREER SERVICESCAREER SERVICES

B U S I N E S S D I R E C T O R Y

SERVICES

Index of Advertisers

Chemir .............................18

Drew University...............19

Eastern Scientific Co.......13

Mass-Vac, Inc.....................6

Micron, Inc. .....................18

NuMega Resonance Labs18

Organix, Inc.....................18

PCI Synthesis.....................4

Rilas Technologies, Inc. ..19

Robertson Microlit Labs..18

Tyger Scientific, Inc. .......18

Waters Corporation..........19


20/20

Check the NESACS home pagefor late Calendar additions:http://www.NESACS.orgNote also the Chemistry Department webpages for travel directions and updates.These include:http://www.bc.edu/schools/cas/chemistry/semina

rs.htmlhttp://www.bu.edu/chemistry/seminars/http://www.brandeis.edu/departments/chemistry/

events/index.htmlhttp://www.chem.harvard.edu/courses/seminars.

phphttp://chemcalendar.mit.edu/index.phphttp://chem.tufts.edu/seminars.htmlhttp://engineering.tufts.edu/chbe/newsEvents/se

minarSeries/index.asphttp://www.chem.umb.eduhttp://www.umassd.edu/cas/chemistry/http://www.uml.edu/Sciences/chemistry/Seminar

s-and-Colloquia.aspxhttp://www.unh.edu/chemistry/events

Mar 3Prof. Bill Tolman (University of Minnesota)Copper Oxygen Intermediates Relevant toMetalloenzymes and Other Oxidation CatalystsBrandeis University, Gerstenzang 1214:00 pm

Mar 4Prof. William B. Tolman (University ofMinnesota)Copper Oxygen Intermediates Relevant toMetalloenzymes and Other Oxidation CatalystsBoston College, Merkert 130 4:00 pm

Prof. Peter Seeberger, (Max Planck Institute)Tufts University, Pearson P-1064:30 pm

Mar 5Prof. William Tolman (University of Minnesota)Boston University, Metcalf Science CenterBuilding, Rm 113 4:00 pm

Mar 6Prof. Karl Gademann (University of Basel) andDr. Chris Senanayake, Boehringer_IngelheimMIT, 6-120 4:00 pm

Mar 10Prof. Ming Hammond (University of California,

Berkeley)Privileged RNA scaffolds for the in vivosensing functionsBrandeis University, Gerstenzang 1214:00 pm

Mar 11Prof. Ming Hammond (University of California,Berkeley)Boston College, Merkert 130 4:00 pm

Prof. Geert-Jan Boons (University of Georgia)Tufts University, Pearson P-1064:30 pm

Mar 12Prof. William D. Jones (University of Rochester)

Why Do Weaker Metal-Carbon Bonds Lead toMore Stable Complexes? What's Going On?Boston College, Merkert 1304:00 PM

Mar 13Prof. Martin Burke (University of Illinois)MIT, 6-120 4:00 pm

Mar 18Prof. Amy E. Keirstead (Univ. of New England)Univ. of New Hampshire, Room N10411:10 am

Mar 20Prof. Jeff Johnson (U. of North Carolina) & Dr.David Kronenthal Bristol Myers Squibb

Mar 21Prof. Connie Lu (University of Minnesota)Harnessing Metal-Metal Bonds: Bonding,Electronic Properties and Small-MoleculeReactivityBrandeis University, Gerstenzang 1214:00 pm

Mar 24Prof. Wenbin Lin (University of Chicago)Brandeis University, Gerstenzang 1214:00 pm

Mar 25Prof. Michael Krische (University of Texas)Boston College, Merkert 130 4:00 pm

Mar 25Prof. Samir Z. Zard (cole Polytechnique,France)MIT, 6-120 4:00 pm

Dr. Grace Wong (Actokine Therapeutics)Career Decisions: Academia vs Industry, andGetting a Foot in the DoorUniv. of New Hampshire, Room N10411:10 am

Mar 27

Prof. Viresh Rawal (University of Chicago)MIT, 6-120 4:00 PM

Professeur Samir Z. Zard, (cole Polytechnique,France)Brandeis University, Gerstenzang 1214:00 PM

Mar 31Prof. Istvan Z. Kiss (Saint Louis University)Brandeis University, Gerstenzang 1214:00 PM

Notices for The NucleusCalendar of Seminarsshould be sent to:

NONPROFITO

RG.

U.S.POSTAGE

PAID

NORTHEASTERN

SECTION

AMERICANCHE

MICAL

SOCIETY

Calendar

19MillRoad

Harvard,MA01451

Northeastern Student Chemistry

Research Conference & Career Symposium

April12-13,2014BostonUniversity

Careerpanels,workshops,researchpresentations,awards&more

Abstract deadline: March 10, 2014

Registration&info:nsycc.orgAbstracts:[email protected]

Hostedby:NortheasternSectionYoungerChemistCommittee(NSYCC)BostonUniversityYoungerChemistCommittee(BUYCC

the nucleus march 2014 issue

Documents