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SupplementF2:TheChemistryofAmino,Nitroso,NitroandRelatedGroups. EditedbySaulPatai Copyright1996JohnWiley&Sons,Ltd. ISBN:0-471-95171-4 Supplement F2 The chemistry of amino, nitroso, nitro and related groups THECHEMISTRY OFFUNCTIONALGROUPS Aseriesofadvancedtreatisesunderthegeneraleditorshipof ProfessorsSaulPataiandZviRappoport Thechemistryofalkenes(2volumes) Thechemistryofthecarbonylgroup(2volumes) Thechemistryoftheetherlinkage Thechemistryoftheaminogroup Thechemistryofthenitroandnitrosogroups(2parts) Thechemistryofcarboxylicacidsandesters Thechemistryofthecarbon nitrogendoublebond Thechemistryofamides Thechemistryofthecyanogroup Thechemistryofthehydroxylgroup(2parts) Thechemistryoftheazidogroup Thechemistryofacylhalides Thechemistryofthecarbon halogenbond(2parts) Thechemistryofthequinonoidcompounds(2volumes,4parts) Thechemistryofthethiolgroup(2parts) Thechemistryofthehydrazo,azoandazoxygroups(2parts) Thechemistryofamidinesandimidates(2volumes) Thechemistryofcyanatesandtheirthioderivatives(2parts) Thechemistryofdiazoniumanddiazogroups(2parts) Thechemistryofthecarbon carbontriplebond(2parts) Thechemistryofketenes,allenesandrelatedcompounds(2parts) Thechemistryofthesulphoniumgroup(2parts) SupplementA:Thechemistryofdouble-bondedfunctionalgroups(2volumes,4parts) SupplementB:Thechemistryofacidderivatives(2volumes,4parts) SupplementC:Thechemistryoftriple-bondedfunctionalgroups(2volumes,3parts) SupplementD:Thechemistryofhalides,pseudo-halidesandazides(2volumes,4parts) SupplementE:Thechemistryofethers,crownethers,hydroxylgroups andtheirsulphuranalogues(2volumes,3parts) SupplementF:Thechemistryofamino,nitrosoandnitrocompoundsandtheirderivatives(2parts) Thechemistryofthemetal carbonbond(5volumes) Thechemistryofperoxides Thechemistryoforganicseleniumandtelluriumcompounds(2volumes) Thechemistryofthecyclopropylgroup(2parts) Thechemistryofsulphonesandsulphoxides Thechemistryoforganicsiliconcompounds(2parts) Thechemistryofenones(2parts) Thechemistryofsulphinicacids,estersandtheirderivatives Thechemistryofsulphenicacidsandtheirderivatives Thechemistryofenols Thechemistryoforganophosphoruscompounds(4volumes) Thechemistryofsulphonicacids,estersandtheirderivatives Thechemistryofalkanesandcycloalkanes SupplementS:Thechemistryofsulphur-containingfunctionalgroups Thechemistryoforganicarsenic,antimonyandbismuthcompounds Thechemistryofenamines(2parts) Thechemistryoforganicgermanium,tinandleadcompounds UPDATES Thechemistryof˛-haloketones,˛-haloaldehydesand˛-haloimines Nitrones,nitronatesandnitroxides Crownethersandanalogs Cyclopropanederivedreactiveintermediates Synthesisofcarboxylicacids,estersandtheirderivatives Thesilicon heteroatombond Synthesesoflactonesandlactams Thesynthesesofsulphones,sulphoxidesandcyclicsulphides Patai’s1992guidetothechemistryoffunctionalgroups SaulPatai C NH C NO C NO 2 2 Supplement F2 The chemistry of amino, nitroso, nitro and related groups Part 1 Edited by SAUL PATAI TheHebrewUniversity,Jerusalem 1996 JOHN WILEY &SONS CHICHESTER NEWYORK BRISBANE TORONTO SINGAPORE AnInterscience(cid:1)R Publication Copyright1996JohnWiley&SonsLtd, BaffinsLane,Chichester, WestSussexPO191UD,England National 01243779777 International(C44)1243779777 e-mail(forordersandcustomerserviceenquiries):[email protected] VisitourHomePageonhttp://www.wiley.co.uk orhttp://www.wiley.com All Rights Reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted,inanyformorbyanymeans,electronic,mechanical,photocopying,recording,scanningor otherwise,except underthetermsoftheCopyright DesignsandPatentsAct1988orundertheterms ofalicenceissuedbytheCopyrightLicensingAgency,90TottenhamCourtRoad,LondonW1P9HE, UK,withoutthepermissioninwritingofthepublisher OtherWileyEditorialOffices JohnWiley&Sons,Inc.,605ThirdAvenue, NewYork,NY10158-0012,USA JacarandaWileyLtd,33ParkRoad,Milton, Queensland4064,Australia JohnWiley&Sons(Canada)Ltd,22WorcesterRoad, Rexdale,OntarioM9W1L1,Canada JohnWiley&Sons(Asia)PteLtd,ClementiLoop#02-01, JinXingDistripark,Singapore129809 LibraryofCongressCataloging-in-PublicationData BritishLibraryCataloguinginPublicationData AcataloguerecordforthisbookisavailablefromtheBritishLibrary ISBN0471951714 Typesetin9/10ptTimesbyLaserWords,Madras,India PrintedandboundinGreatBritainbyBiddlesLtd,Guildford,Surrey Thisbookisprintedonacid-freepaperresponsiblymanufacturedfromsustainableforestation,for whichatleasttwotreesareplantedforeachoneusedforpaperproduction. Contributing authors PinchasAped Department of Chemistry, Bar-Ilan University, Ramat- Gan 52900,Israel ShmuelBittner Institutes for Applied Research and Department of Chemistry, Ben-Gurion University of the Negev, Beer- Sheva 84105, Israel RichardD.Bowen Chemistry and Chemical Technology, University of Bradford, Bradford, West YorkshireBD7 1DP, UK G. V.Boyd Department of Organic Chemistry, The Hebrew Univer- sity of Jerusalem, Jerusalem 91904, Israel SilviaBradamante Universita´ degli Studi di Milano, CNR, Centro di Studio sullaSintesieStereochimicadiSpecialiSistemiOrganici, viaGolgi 19, 20133 Milano,Italy MaryStinecipherCampbell DX-2 Explosive Science Technology, MS C920, Los Alamos National Laboratory, Los Alamos, New Mexico 87545-0000,USA LarsCarlsen Department of Environmental Chemistry, National Environmental Research Institute, P.O.Box 358, Fred- eriksborgvej 399, DK-4000 Roskilde, Denmark H.K.Chagger Department of Fuel and Energy, University of Leeds, Leeds LS2 9JT, UK Y.L.Chow Department of Chemistry, Simon Fraser University, Burnaby, British Columbia V5A 1S6, Canada HelgeEgsgaard EnvironmentalScienceandTechnologyDepartment,Risø National Laboratory, DK-4000 Roskilde, Denmark PeterEyer Walther-Straub-Institut fu¨r Pharmakologie und Toxikolo- gie der Ludwig-Maximilians-Universita¨t Mu¨nchen, Nussbaumstrasse26, D-80336 Mu¨nchen, Germany LucianoForlani Universita`diBologna,DipartimentodiChimicaOrganica ‘A. Mangini’,vialeRisorgimento4,40136Bologna,Italy AlbertJ.Fry Department of Chemistry, Wesleyan University, Middle- town,Connecticut 06459,USA D.Gallemann Walther-Straub-Institut fu¨r Pharmakologie und Toxikolo- gie der Ludwig-Maximilians-Universita¨t Mu¨nchen, Nussbaumstrasse26, D-80336 Mu¨nchen, Germany T. I.Ho National Taiwan University, Department of Chemistry, Roosevelt Road, Sec. 4, Taipei, Taiwan, Republic of China v vi Contributingauthors William M. Horspool Department of Chemistry, The University of Dundee, DundeeDD1 4HN, Scotland JoelF. Liebman Department of Chemistry and Biochemistry, University of Maryland, Baltimore County Campus, 1000 Hilltop Circle, Baltimore, Maryland 21250,USA AlanH.Mehler 10401 Grosvenor Place, Apt. 404, Rockville, Maryland 20852,USA ChristianaA.Mitsopoulou Department of Chemistry, University of Athens, 15771 Athens,Greece NormaS.Nudelman Universidad de Buenos Aires, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, 1428 Buenos Aires, Argentina PaulRademacher Institut fu¨r organische Chemie der Universita¨t Essen, D-45117 Essen, Germany EdwardW. Randall Department of Chemistry, Queen Mary and Westfield College, MileEnd Road, London E1 4NS, UK J.P.B.Sandall University of Exeter, Department of Chemistry, Chem- istry Building,Stocker Road, Exeter EX4 4QD, UK HanochSenderowitz Department of Chemistry, Columbia University, New York,NY 10027, USA JohnShorter SchoolofChemistry,University,ofHull,HullHU67RX, UK SuzanneW.Slayden Department of Chemistry, George Mason University, 4400 University Drive, Fairfax, Virginia 22030-4444, USA HowardE.Smith Department of Chemistry, Vanderbilt University, Nash- ville,Tennessee 37235, USA SalvatoreSorriso Dipartimento di Chimica, Universita` di Perugia, via Elce di sotto 10, 06100 Perugia, Italy KennethC. Westaway Department of Chemistry and Biochemistry, Laurentian University, Ramsey Lake Road, Sudbury, Ontario, Canada P3E 2C6 A.Williams Department of Fuel and Energy, University of Leeds, Leeds LS2 9JT, UK D.LynH. Williams UniversityofDurham,DepartmentofChemistry,Science Laboratories,South Road, Durham DH1 3LE, UK JacobZabicky Institutes for Applied Research and Department of Chemistry, Ben-Gurion University of the Negev, Beer- Sheva 84105, Israel HeinrichZollinger Technisch-Chemisches Laboratorium, ETH-Zentrum, CH-8092 Zu¨rich, Switzerland Foreword The material reviewed in the present volume Supplement F2: The chemistry of amino, nitroso,nitroandrelatedgroups has been previously covered in the following books in the Chemistry of the Functional Groups series: The chemistry of the amino group (1968); The chemistry of the nitro and nitroso groups,Parts 1 and 2 (1969); SupplementF:Thechemistryofamino,nitrosoandnitrocompoundsandtheirderiva- tives,Parts 1 and 2 (1982). Nitrones,nitronates and nitroxides (‘Update’ volume, 1989). The chapters in this Supplement F2 generally contain references up to the middle of 1995.Oftheplannedcontentsofthisbook,onlythreechaptersfailedtomaterialize.These were on NQR and ESR, on pyrolysis, and on photoinduced electron transfer reactions. I hope that these missing subjects will be dealt with in a later forthcoming supplementary volume of the series. I would be very grateful to any reader who would communicate to me comments or criticisms regarding the contents or the presentation of this volume. Jerusalem SAUL PATAI June 1996 vii The Chemistry of Functional Groups Preface to the series The series ‘The Chemistry of Functional Groups’ was originally planned to cover in each volume all aspects of the chemistry of one of the important functional groups in organicchemistry.Theemphasisislaidonthepreparation,propertiesandreactionsofthe functionalgrouptreatedandontheeffectswhichitexertsbothintheimmediatevicinity of the group in question and in thewhole molecule. A voluntary restriction on the treatment of the various functional groups in these volumes is that material included in easily and generally available secondary or ter- tiarysources,suchasChemicalReviews,QuarterlyReviews,OrganicReactions,various ‘Advances’and‘Progress’seriesandintextbooks(i.e.inbookswhichareusuallyfound inthechemicallibrariesofmostuniversitiesandresearchinstitutes),shouldnot,asarule, berepeatedindetail,unlessitisnecessaryforthebalancedtreatmentofthetopic.There- fore each of the authors is asked not to give an encyclopaedic coverage of his subject, buttoconcentrateonthemostimportantrecentdevelopmentsandmainlyonmaterialthat has not been adequately covered by reviews or other secondary sources by the time of writingofthechapter,andtoaddresshimselftoareaderwhoisassumedtobeatafairly advanced postgraduatelevel. Itisrealizedthatnoplancanbedevisedforavolumethatwouldgiveacompletecov- erageofthefieldwithnooverlapbetweenchapters,whileatthesametimepreservingthe readabilityofthetext.TheEditorssetthemselvesthegoalofattainingreasonablecoverage withmoderateoverlap,withaminimumofcross-referencesbetweenthechapters.Inthis manner,sufficientfreedomisgiventotheauthorstoproducereadablequasi-monographic chapters. The general plan of each volume includes the following main sections: (a) Anintroductorychapterdealswiththegeneralandtheoreticalaspectsofthe group. (b) Chapters discuss the characterization and characteristics of the functional groups, i.e.qualitativeandquantitativemethodsofdeterminationincludingchemicalandphysical methods, MS, UV, IR, NMR, ESR and PES as well as activating and directive effects exerted by the group, and its basicity, acidity and complex-forming ability. (c) One or more chapters deal with the formation of the functional group in question, eitherfromothergroupsalreadypresentinthemoleculeorbyintroducingthenewgroup directly or indirectly. This is usually followed by a description of the synthetic uses of the group, includingits reactions, transformations and rearrangements. (d) Additional chapters deal with special topics such as electrochemistry, photochem- istry, radiation chemistry, thermochemistry, syntheses and uses of isotopically labelled compounds,aswellaswithbiochemistry,pharmacologyandtoxicology.Wheneverappli- cable, unique chapters relevant only to single functional groups are also included (e.g. ‘Polyethers’, ‘Tetraaminoethylenes’ or ‘Siloxanes’). ix x Preface to the series Thisplan entails that thebreadth, depth and thought-provokingnatureof each chapter willdifferwiththeviewsandinclinationsoftheauthorsandthepresentationwillneces- sarilybesomewhatuneven.Moreover,aseriousproblemiscausedbyauthorswhodeliver their manuscript late or not at all. In order to overcome this problem at least to some extent, some volumes may be published without giving consideration to the originally planned logical order of the chapters. Since the beginning of the Series in 1964, two main developments have occurred. The first of these is the publication of supplementary volumes which contain material relating to several kindred functional groups (Supplements A, B, C, D, E, F and S). The second ramification is the publication of a series of ‘Updates’, which contain in each volume selected and related chapters, reprinted in the original form in which they were published,togetherwithanextensiveupdatingofthesubjects,ifpossible,bytheauthors of the original chapters. A complete list of all above mentioned volumes published to date will be found on the page opposite the inner title page of this book. Unfortunately, the publicationof the ‘Updates’ has been discontinuedfor economic reasons. Advice or criticism regarding the plan and execution of this series will be welcomed by the Editors. The publication of this series would never have been started, let alone continued, withoutthesupportofmanypersonsinIsraelandoverseas,includingcolleagues,friends and family. The efficient and patient co-operation of staff-members of the publisheralso rendered us invaluableaid. Our sincere thanks are due to all of them. The Hebrew University SAUL PATAI Jerusalem, Israel ZVI RAPPOPORT Contents 1 Molecular mechanics calculations 1 Pinchas ApedandHanoch Senderowitz 2 Structuralchemistry 85 SalvatoreSorriso 3 Chiropticalpropertiesof amino compounds 105 HowardE.Smith 4 Photoelectronspectraof amines, nitrosoandnitrocompounds 159 Paul Rademacher 5 Thechemistryofionized,protonatedandcationatedaminesinthe gasphase 205 RichardD.Bowen 6 Massspectrometryofnitroandnitrosocompounds 249 Helge EgsgaardandLarsCarlsen 7 NMR ofcompounds containing (cid:1)NH ,(cid:1)NO and (cid:1)NOgroups 295 2 2 EdwardW. RandallandChristianaA. Mitsopoulou 8 Thermochemistryofamines,nitrosocompounds,nitrocompounds andrelatedspecies 337 Joel F. Liebman, Mary Stinecipher Campbell and Suzanne W. Slayden 9 Acidityandbasicity 379 SilviaBradamante 10 Hydrogen bonding and complex formation involving compounds withamino, nitrosoandnitrogroups 423 LucianoForlani 11 Electroniceffectsofnitro,nitroso,amino andrelatedgroups 479 JohnShorter 12 Advancesinthechemistryof aminoand nitrocompounds 533 G. V.Boyd 13 Diazotizationofamines anddediazoniationof diazoniumions 627 Heinrich Zollinger xi
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