Table Of ContentStereochemistry and Global Connectivity:
The Legacy of Ernest L. Eliel
Volume 2
1258
ACS SYMPOSIUM SERIES
Stereochemistry and Global Connectivity:
The Legacy of Ernest L. Eliel
Volume 2
H. N. Cheng, Editor
U.S.DepartmentofAgriculture,NewOrleans,Lousiana
Cynthia A. Maryanoff, Editor
BaruchS.BlumbergInstitute,Doylestown,Pennsylvania
Bradley D. Miller, Editor
ACSInternationalActivities, Washington, DC
Diane Grob Schmidt, Editor
UniversityofCincinnati, Cincinnati, Ohio
Sponsored by the
ACS Division of Organic Chemistry
AmericanChemicalSociety,Washington,DC
DistributedinprintbyOxfordUniversityPress
LibraryofCongressCataloging-in-PublicationData
Names:Cheng,H.N.,editor.|AmericanChemicalSociety.DivisionofOrganic
Chemistry.
Title:Stereochemistryandglobalconnectivity:thelegacyofErnestL.Eliel
Volume2/H.N.Cheng,editor(U.S.DepartmentofAgriculture,NewOrleans,
Lousiana)[andthreeothers];sponsoredbytheACSDivisionofOrganic
Chemistry.
Description:Washington,DC:AmericanChemicalSociety,[2017]-|Series:
ACSsymposiumseries;1258|Includesbibliographicalreferencesand
index.
Identifiers:LCCN2017045040(print)|LCCN2017050615(ebook)|ISBN
9780841232372(ebook)|ISBN9780841232389(v.1)|ISBN9780841232402(v.2)
Subjects:LCSH:Stereochemistry.|Communicationinscience.|Conformational
analysis.|Eliel,ErnestL.(ErnestLudwig),1921-2008.
Classification:LCCQD481(ebook)|LCCQD481.S75742017(print)|DDC
547/.1223--dc23
LCrecordavailableathttps://lccn.loc.gov/2017045040
ThepaperusedinthispublicationmeetstheminimumrequirementsofAmericanNational
Standard for Information Sciences—Permanence of Paper for Printed Library Materials,
ANSIZ39.48n1984.
Copyright©2017AmericanChemicalSociety
DistributedinprintbyOxfordUniversityPress
AllRightsReserved. ReprographiccopyingbeyondthatpermittedbySections107or108
oftheU.S.CopyrightActisallowedforinternaluseonly,providedthataper-chapterfeeof
$40.25plus$0.75perpageispaidtotheCopyrightClearanceCenter,Inc.,222Rosewood
Drive,Danvers,MA01923,USA.Republicationorreproductionforsaleofpagesinthis
bookispermittedonlyunderlicensefromACS.Directtheseandotherpermissionrequests
toACSCopyrightOffice,PublicationsDivision,115516thStreet,N.W.,Washington,DC
20036.
Thecitationoftradenamesand/ornamesofmanufacturersinthispublicationisnottobe
construedasanendorsementorasapprovalbyACSofthecommercialproductsorservices
referenced herein; nor should the mere reference herein to any drawing, specification,
chemicalprocess, orotherdataberegardedasalicenseorasaconveyanceofanyright
or permission to the holder, reader, or any other person or corporation, to manufacture,
reproduce,use,orsellanypatentedinventionorcopyrightedworkthatmayinanywaybe
relatedthereto. Registerednames,trademarks,etc.,usedinthispublication,evenwithout
specificindicationthereof,arenottobeconsideredunprotectedbylaw.
PRINTEDINTHEUNITEDSTATESOFAMERICA
Foreword
The ACS Symposium Series was first published in 1974 to provide a
mechanism for publishing symposia quickly in book form. The purpose of
the series is to publish timely, comprehensive books developed from the ACS
sponsoredsymposiabasedoncurrentscientificresearch. Occasionally,booksare
developed from symposia sponsored by other organizations when the topic is of
keeninteresttothechemistryaudience.
Beforeagreeingtopublishabook,theproposedtableofcontentsisreviewed
forappropriateandcomprehensivecoverageandforinteresttotheaudience. Some
papersmaybeexcludedtobetterfocusthebook;othersmaybeaddedtoprovide
comprehensiveness. When appropriate, overview or introductory chapters are
added. Draftsofchaptersarepeer-reviewedpriortofinalacceptanceorrejection,
andmanuscriptsarepreparedincamera-readyformat.
As a rule, only original research papers and original review papers are
included in the volumes. Verbatim reproductions of previous published papers
arenotaccepted.
ACSBooksDepartment
Contents
Foreword.......................................................................................................................... ix
InMemoryofErnestEliel.............................................................................................. xi
Preface............................................................................................................................xiii
StereochemistryofOrganicCompounds
1. TheoreticalEvidencefortheRelevanceofn(S)→σ*(C-P),σ(C-S)→
σ*(C-P),andn(F)→σ*(C-X)(X=H,C,O,S)StereoelectronicInteractions .... 3
EusebioJuaristiandRafaelNotario
2. TheImportanceofElectrostaticInteractionsontheConformational
BehaviorofSubstituted1,3-Dioxanes:TheCaseof5-Phenyl-1,3-dioxane ...... 19
WilliamF.BaileyandKyleM.Lambert
3. AsymmetricAutocatalysisandtheOriginofHomochirality............................. 27
KensoSoaiandArimasaMatsumoto
4. InterplaybetweenOrganocatalysisandMulticomponentReactionsin
StereoselectiveSynthesis........................................................................................ 49
DanielG.RiveraandMárcioW.Paixão
5. SyntheticApproachestotheStereochemicallyComplexAntitumorDrug
Ecteinascidin-743: AMarineNaturalProductbytheNameYondelis®or
Trabectidin.............................................................................................................. 61
PlatoA.Magriotis
6. CondensationReactionbetweenPhenanthroline-5,6-dionesand
EthylenediamineandItsOptimizationthroughDialoguebetweenTheory
andExperiment...................................................................................................... 79
LuisSanhueza,DiegoCortés,IvánGonzález,andBárbaraLoeb
7. SolventEffectsonElectronicCircularDichroismSpectra ................................ 91
Aguinaldo Robinson de Souza, Valdecir Farias Ximenes, and
NelsonHenriqueMorgon
vii
NMR Applications
8. ErnestL.Eliel,aPhysicalOrganicChemistwiththeRightToolfortheJob:
RapidInjectionNuclearMagneticResonance .................................................. 105
AndyA.ThomasandScottE.Denmark
9. CharacterizationofMaterialswithNMRSpectroscopy .................................. 135
CecilDybowski
10. FromNMRSpectratoMolecularStructuresandConformation ................... 161
AlanE.Tonelli
11. SolutionNMRStructureandConformationofSilkFibroinsStoredin
BombyxmoriandSamiacynthiariciniSilkworms ............................................ 191
TetsuoAsakura,YuSuzuki,andAkioNishimura
12. NovelPolymericProductsDerivedfromBiodiesel ........................................... 207
AtanuBiswas,ZengsheLiu,RoselayneFurtado,CarlucioR.Alves,andH.N.Cheng
Editors’Biographies .................................................................................................... 221
Indexes
AuthorIndex ................................................................................................................ 225
SubjectIndex................................................................................................................ 227
viii
Foreword
A major strength of American Chemical Society (ACS) is the large number of
volunteers who help to grow and sustain the organization, from local sections to
technical divisions, from regional to national meetings, from task forces to national
committees, andfromconductingresearchtowritingandreviewingmanuscriptsfor
journals. SomeofthemspendliterallythousandsofhoursonbehalfofACSandthe
globalchemistryenterprise,helpingstudentsorfellowscientists,organizingmeetings
and symposia, reaching out to the local communities, publicizing the benefits of
science,andconnectingwithglobalcolleaguesandpartners.
One of the people who excelled in these efforts was the late Prof. Ernest L.
Eliel. FormanyyearshetaughtattheUniversityofNotreDameandtheUniversity
of North Carolina and was an acknowledged leader in organic stereochemistry and
conformational analysis. He was also a leader at ACS, serving as ACS President
in 1992 and Chair of ACS Board of Directors in 1987-89. He initiated several
international activities, particularly with respect to Latin America. I had worked
withhimonmanyoccasions,andhewasalwayscourteous,judicious,analytical,and
thoughtful.
UnfortunatelyProf. Elielleftusin2008. AsACSImmediatePastPresidentin
2016,itwasmypleasuretobeassociatedwithasymposiumorganizedbyDr. Cynthia
MaryanoffandmeattheACSNationalMeetinginPhiladelphiainhonorofProf.Eliel.
Becauseofthesuccessofthesymposium,Dr.MaryanoffandIdecidedtoteamupwith
Dr. H.N.ChengandDr. BradleyMillertoeditabookhighlightingstereochemistry
andglobalconnectivity,whichrepresentedtwoofthekeylegaciesofProf. Eliel. We
wereverypleasedthatsomanyofouracademiccolleagueswerewillingtoparticipate
in this project in honor of Prof. Eliel. Thanks are due to all of the authors and my
co-editorsfortheirwonderfulefforts.
Because stereochemistry is a fundamental chemistry concept, ongoing research
is carried out in different subfields of chemistry (such as organic, medicinal,
carbohydrates, polymers), using various analytical techniques (such as NMR, X-ray
crystallography, and circular dichroism). The two volumes of this book contain
many research papers that represent cutting-edge research in all the above areas.
Becausechemistryisnowaworld-wideenterprise,globalconnectivityisimportantto
chemistrypractitioners,andthechaptersoninternationalactivitiesshouldbeofgreat
interestaswell. Hopefullythereaderswillfindthesetwobookvolumesusefultothem
in their research or professional work, and the example of Prof. Eliel will motivate
themtovolunteertheirtimeandtalenttoACSandtheglobalchemistryenterprise!
DianeGrobSchmidt
2015ACSPresident
ix
