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dc.contributor.authorSmith, Graham
dc.contributor.authorWermuth, Urs D
dc.date.accessioned2017-05-03T13:51:14Z
dc.date.available2017-05-03T13:51:14Z
dc.date.issued2011
dc.date.modified2012-04-09T23:18:47Z
dc.identifier.issn1074-1542
dc.identifier.doi10.1007/s10870-011-0186-4
dc.identifier.urihttp://hdl.handle.net/10072/44320
dc.description.abstractThe structures of two hydrated proton-transfer compounds of 4-piperidinecarboxamide (isonipecotamide) with the isomeric heteroaromatic carboxylic acids indole-2-carboxylic acid and indole-3-carboxylic acid, namely 4-carbamoylpiperidinium indole-2-carboxylate dihydrate (1) and 4-carbamoylpiperidinium indole-3-carboxylate hemihydrate (2) have been determined at 200 K. Crystals of both 1 and 2 are monoclinic, space groups P21/c and P2/c, respectively with Z = 4 in cells having dimensions a = 10.6811(4), b = 12.2017(4), c = 12.5456(5) Ŭ ߠ= 96.000(4)ࠨ1) and a = 15.5140(4), b = 10.2908(3), c = 9.7047(3) Ŭ ߠ= 97.060(3)ࠨ2). Hydrogen-bonding in 1 involves a primary cyclic interaction involving complementary cation amide N-H緷O(carboxyl) anion and anion hetero N-H緷O(amide) cation hydrogen bonds [graph set R22(9)]. Secondary associations involving also the water molecules of solvation give a two-dimensional network structure which includes weak water O-H緷p interactions. In the three-dimensional hydrogen-bonded structure of 2, there are classic centrosymmetric cyclic head-to-head hydrogen-bonded amide-amide interactions [graph set R22(8)] as well as lateral cyclic amide-O linked amide-amide extensions [graph set R42(8)]. The anions and the water molecule, which lies on a twofold rotation axis, are involved in secondary extensions.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.languageEnglish
dc.language.isoeng
dc.publisherSpringer
dc.publisher.placeUnited States
dc.relation.ispartofstudentpublicationN
dc.relation.ispartofpagefrom1850
dc.relation.ispartofpageto1854
dc.relation.ispartofissue12
dc.relation.ispartofjournalJournal of Chemical Crystallography
dc.relation.ispartofvolume41
dc.rights.retentionY
dc.subject.fieldofresearchPhysical chemistry
dc.subject.fieldofresearchcode3406
dc.titleHydrogen-Bonding in the Structures of the Hydrated Proton-Transfer Compounds of Isonipecotamide with the Isomeric Indole-2- and Indole-3-Carboxylic Acids
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.date.issued2011
gro.hasfulltextNo Full Text
gro.griffith.authorWermuth, Urs D.


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