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diamine wikipedia jump to content main menu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 practical considerations 2 aliphatic diamines toggle aliphatic diamines subsection 2 1 linear 2 2 branched 2 3 cyclic 2 4 xylylenediamines 3 aromatic diamines 4 geminal diamines 5 references 6 external links toggle the table of contents diamine 15 languages العربية català čeština deutsch español euskara français magyar 日本語 polski português română русский 粵語 中文 edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia amine with two amino groups for the ink company see diamine inks limited general structure of primary diamines the primary amino groups nh 2 are marked blue r is a divalent organic radical e g a para phenylene group a diamine is an amine with two amino groups diamines are used as monomers to prepare polyamides polyimides and polyureas the term diamine refers mostly to primary diamines as those are the most reactive 1 2 practical considerations edit in terms of quantities produced 1 6 diaminohexane a precursor to nylon 6 6 is most important followed by ethylenediamine 3 vicinal diamines 1 2 diamines are a structural motif in many biological compounds and are used as ligands in coordination chemistry 4 many diamines are used as hardeners in the curing of epoxide resins putrescine and cadaverine are simple diamines that occur widely in nature aliphatic diamines edit linear edit 2 carbon backbone ethylenediamine 1 2 diaminoethane related derivatives include the n alkylated compounds 1 1 dimethylethylenediamine 1 2 dimethylethylenediamine ethambutol tetrakis dimethylamino ethylene tmeda many 1 2 diamine derivatives are of practical interest such as penicillin 5 6 ethylenediamine 3 carbon backbone 1 3 diaminopropane propane 1 3 diamine 4 carbon backbone putrescine butane 1 4 diamine 5 carbon backbone cadaverine pentane 1 5 diamine cadaverine 6 carbon backbone hexamethylenediamine hexane 1 6 diamine hmd hmd and other long chain diamines can be prepared by hydrocyanation to give di nitrile which can be hydrogenated 7 branched edit derivatives of ethylenediamine are prominent 1 2 diaminopropane which is chiral 2 3 butanediamine two diastereomers one of which is c 2 symmetric diphenylethylenediamine two diastereomers one of which is c 2 symmetric trimethylhexamethylenediamine several isomers 1 2 diaminocyclohexane two diastereomers one of which is c 2 symmetric cyclic edit 1 4 diazacycloheptane piperazine ch 2 ch 2 nh 2 1 4 diazacycloheptane xylylenediamines edit xylylenediamines are classified as alkylamines since the amine is not directly attached to an aromatic ring o xylylenediamine or oxd m xylylenediamine or mxd p xylylenediamine or pxd aromatic diamines edit three phenylenediamines are known 8 o phenylenediamine or opd m phenylenediamine or mpd p phenylenediamine or ppd 2 5 diaminotoluene is related to ppd but contains a methyl group on the ring p phenylenediamine various n methylated derivatives of the phenylenediamines are known dimethyl 4 phenylenediamine a reagent n n di 2 butyl 1 4 phenylenediamine an antioxidant examples with two aromatic rings include derivatives of biphenyl and naphthalene 4 4 diaminobiphenyl 1 8 diaminonaphthalene structure of wurster s cation illustrating the ability of amino substituents to stabilize arene radical cations geminal diamines edit bis dimethylamino methane geminal diamines 1 1 diamines are an uncommon class of diamines mainly of academic interest of the few that exist most are di tertiary amines bis dimethylamino methane ch 3 2 n 2 ch 2 is an isolable example geminal diamines with n h bonds are particularly rare they are invoked as intermediates in transamination reactions and the reduction of amidines in aqueous conditions they preferentially eliminate the less basic amine to leave an iminium ion 9 some stable geminal diamines have been isolated 10 the parent gem diamine is methylenediamine diaminomethane which again is mainly of theoretical interest references edit lucet denis le gall thierry mioskowski charles 1998 the chemistry of vicinal diamines angewandte chemie international edition 37 19 2580 2627 doi 10 1002 sici 1521 3773 19981016 37 19 2580 aid anie2580 3 0 co 2 l pmid 29711625 nucleophilicity trends of amines master organic chemistry 2018 05 07 retrieved 2019 08 18 peter roose karsten eller erhard henkes roland rossbacher hartmut höke 2005 amines aliphatic ullmann s encyclopedia of industrial chemistry weinheim wiley vch pp 1 55 doi 10 1002 14356007 a02_001 pub2 isbn 3 527 30673 0 lucet denis le gall thierry mioskowski charles 1998 the chemistry of vicinal diamines angewandte chemie international edition 37 19 2580 2627 doi 10 1002 sici 1521 3773 19981016 37 19 2580 aid anie2580 3 0 co 2 l pmid 29711625 saibabu kotti s r s timmons cody li guigen 2006 vicinal diamino functionalities as privileged structural elements in biologically active compounds and exploitation of their synthetic chemistry chemical biology drug design 67 2 101 114 doi 10 1111 j 1747 0285 2006 00347 x pmid 16492158 lucet denis le gall thierry mioskowski charles 1998 the chemistry of vicinal diamines angewandte chemie international edition 37 19 2580 2627 doi 10 1002 sici 1521 3773 19981016 37 19 2580 aid anie2580 3 0 co 2 l pmid 29711625 dahlmann marc grub joachim löser eckhard 2011 butadiene ullmann s encyclopedia of industrial chemistry pp 1 24 doi 10 1002 14356007 a04_431 pub2 isbn 978 3 527 30673 2 robert a smiley phenylene and toluenediamines in ullmann s encyclopedia of industrial chemistry 2002 wiley vch weinheim doi 10 1002 14356007 a19_405 moad graeme benkovic s j 1 august 1978 on the mechanism of decomposition of geminal diamines journal of the american chemical society 100 17 5495 5499 bibcode 1978jachs 100 5495m doi 10 1021 ja00485a038 issn 0002 7863 aydın fatma arslan n burcu 5 september 2021 synthesis spectral properties crystal structure and theoretical calculations of a new geminal diamine 2 2 2 trichloro n n bis 2 nitrophenyl ethane 1 1 diamine journal of molecular structure 1232 129976 bibcode 2021jmost123229976a doi 10 1016 j molstruc 2021 129976 external links edit diamines at the u s national library of medicine medical subject headings mesh synthesis of diamines retrieved from https en wikipedia org w index php title diamine oldid 1362775560 categories diamines monomers hidden categories articles with short description short description is different from wikidata this page was last edited on 6 july 2026 at 03 16 utc page was rendered with parsoid text is available under the creative commons attribution sharealike 4 0 license additional terms may apply by using this site you agree to the terms of use and privacy policy wikipedia is a registered trademark of the wikimedia foundation inc a non profit organization privacy policy about wikipedia disclaimers contact wikipedia legal safety contacts code of conduct developers statistics cookie statement mobile view search search toggle the table of contents diamine 15 languages add topic