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Structure and crystal packing of 4-aminobenzonitriles and 4-amino-3,5-dimethylbenzonitriles at various temperatures

dc.contributor.authorHeine, Andreas
dc.contributor.authorHerbst-Irmer, Regine
dc.contributor.authorStalke, Dietmar
dc.contributor.authorKühnle, Wolfgang
dc.contributor.authorZachariasse, Klaas A.
dc.date.accessioned2009-07-03T12:36:17Z
dc.date.available2009-07-03T12:36:17Z
dc.date.issued1994
dc.identifier.citationHeine, Andreas; Herbst-Irmer, Regine; Stalke, Dietmar; Kühnle, Wolfgang; Zachariasse, Klaas A. (1994): Structure and crystal packing of 4-aminobenzonitriles and 4-amino-3,5-dimethylbenzonitriles at various temperatures - Acta Crystallographica / B, Vol. 50, Nr. 3, p.363-373
dc.identifier.urihttp://resolver.sub.uni-goettingen.de/purl?goescholar/3406
dc.description.abstractThe amino N atom in 4-aminobenzonitrile (ABN) and 4-(dimethylamino)benzonitrile (DMABN) has a pyramidal character, with values of 34(3) and 11.9 (3) c~, respectively, for the angle between the planes of the amino group and the phenyl ring. In 3,5-dimethyl-4-(dimethylamino)benzonitrile (MMD) at 173 K, the dimethylamino group is twisted over an angle of 59.3 (2) "~ with respect to the phenyl plane. In addition, the amino N(1) atom is not located in the plane of the phenyl ring, with an out-of-plane displacement of 0.117 (5)/~. The N-phenyl bond length in MMD of 1.414 (3)/~ is larger that that in the four other aminobenzonitriles, for which an average bond length of 1.367,~ is found. With DMABN, the crystal structure consists of stacks with an alternating orientation of the molecules. In the crystals of ABN, 3,5-dimethyl-4-(methylamino)benzonitrile (MHD) and 4-amino-3,5-dimethylbenzonitrile (HHD), hydrogen bonding is an important structural element. In ABN and MHD, hydrogen bonds are formed between an amino H atom and the cyano N atom of adjacent molecules. In HHD, each H atom is linked to a cyano N atom of two different neighbouring molecules, in a layered structure consisting of squares and octagons. Temperature-dependent solid-solid phase transitions are observed with all five aminobenzonitriles studied here. Crystals of the low-temperature phase could only be obtained from ABN, with lattice constants which are considerably different from those observed at room temperature.
dc.format.mimetypeapplication/pdf
dc.language.isoeng
dc.identifier.bibliographicCitationActa Crystallographica / B;Vol. 50, Nr. 3, p.363-373
dc.rightsopenAccess
dc.rights.urihttp://goedoc.uni-goettingen.de/goescholar/License_Goedoc_2009_03.txt
dc.subjectanorganische Chemie
dc.subject.ddc540
dc.titleStructure and crystal packing of 4-aminobenzonitriles and 4-amino-3,5-dimethylbenzonitriles at various temperatures
dc.typejournalArticle
dc.identifier.doi10.1107/S0108768193008523
dc.type.versionpublishedVersion
dc.bibliographicCitation.volume50
dc.bibliographicCitation.issue3
dc.bibliographicCitation.firstPage363
dc.bibliographicCitation.lastPage373
dc.type.subtypejournalArticle
dc.description.statuspeerReviewed
dc.bibliographicCitation.journalActa Crystallographica / B


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