The hydrogen-bonding patterns of 3-phenylpropylammonium benzoate and 3-phenylpropylammonium 3-iodobenzoate: generation of chiral crystals from achiral molecules

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dc.contributor.authorLemmerer, Andreas
dc.date.accessioned2018-03-15T13:56:48Z
dc.date.available2018-03-15T13:56:48Z
dc.date.issued2008
dc.date.updated2016-01-20T09:38:43Z
dc.description.abstractThe crystal structures and hydrogen-bonding patterns of 3-phenyl­propyl­ammonium benzoate, C9H14N+·C7H5O2-, (I), and 3-phenyl­propyl­ammonium 3-iodo­benzoate, C9H14N+·C7H4IO2-, (II), are reported and compared. The addition of the I atom on the anion in (II) produces a different hydrogen-bonding pattern to that of (I). In addition, the supra­molecular heterosynthon of (II) produces a chiral crystal packing not observed in (I). Compound (I) packs in a centrosymmetric fashion and forms achiral one-dimensional hydrogen-bonded columns through charge-assisted N-H...O hydrogen bonds. Compound (II) packs in a chiral space group and forms helical one-dimensional hydrogen-bonded columns with 21 symmetry, consisting of repeating R43(10) hydrogen-bonded rings that are commonly observed in ammonium carboxyl­ate salts con­tain­ing chiral mol­ecules. This hydrogen-bond pattern, which has been observed repeatedly in ammonium carboxyl­ate salts, thus provides a means of producing chiral crystal structures from achiral mol­ecules.
dc.identifierhttp://dx.doi.org/10.1107/S0108270108036500
dc.identifier.apacitationLemmerer, A. (2008). The hydrogen-bonding patterns of 3-phenylpropylammonium benzoate and 3-phenylpropylammonium 3-iodobenzoate: generation of chiral crystals from achiral molecules. <i>Acta Crystallographica Section C-Crystal Structure Communications</i>, http://hdl.handle.net/11427/27668en_ZA
dc.identifier.chicagocitationLemmerer, Andreas "The hydrogen-bonding patterns of 3-phenylpropylammonium benzoate and 3-phenylpropylammonium 3-iodobenzoate: generation of chiral crystals from achiral molecules." <i>Acta Crystallographica Section C-Crystal Structure Communications</i> (2008) http://hdl.handle.net/11427/27668en_ZA
dc.identifier.citationLemmerer, A. (2008). The hydrogen-bonding patterns of 3-phenylpropylammonium benzoate and 3-phenylpropylammonium 3-iodobenzoate: generation of chiral crystals from achiral molecules. Acta Crystallographica Section C: Crystal Structure Communications, 64(12), 626-629.
dc.identifier.ris TY - Journal Article AU - Lemmerer, Andreas AB - The crystal structures and hydrogen-bonding patterns of 3-phenyl­propyl­ammonium benzoate, C9H14N+·C7H5O2-, (I), and 3-phenyl­propyl­ammonium 3-iodo­benzoate, C9H14N+·C7H4IO2-, (II), are reported and compared. The addition of the I atom on the anion in (II) produces a different hydrogen-bonding pattern to that of (I). In addition, the supra­molecular heterosynthon of (II) produces a chiral crystal packing not observed in (I). Compound (I) packs in a centrosymmetric fashion and forms achiral one-dimensional hydrogen-bonded columns through charge-assisted N-H...O hydrogen bonds. Compound (II) packs in a chiral space group and forms helical one-dimensional hydrogen-bonded columns with 21 symmetry, consisting of repeating R43(10) hydrogen-bonded rings that are commonly observed in ammonium carboxyl­ate salts con­tain­ing chiral mol­ecules. This hydrogen-bond pattern, which has been observed repeatedly in ammonium carboxyl­ate salts, thus provides a means of producing chiral crystal structures from achiral mol­ecules. DA - 2008 DB - OpenUCT DP - University of Cape Town J1 - Acta Crystallographica Section C-Crystal Structure Communications LK - https://open.uct.ac.za PB - University of Cape Town PY - 2008 T1 - The hydrogen-bonding patterns of 3-phenylpropylammonium benzoate and 3-phenylpropylammonium 3-iodobenzoate: generation of chiral crystals from achiral molecules TI - The hydrogen-bonding patterns of 3-phenylpropylammonium benzoate and 3-phenylpropylammonium 3-iodobenzoate: generation of chiral crystals from achiral molecules UR - http://hdl.handle.net/11427/27668 ER - en_ZA
dc.identifier.urihttp://hdl.handle.net/11427/27668
dc.identifier.vancouvercitationLemmerer A. The hydrogen-bonding patterns of 3-phenylpropylammonium benzoate and 3-phenylpropylammonium 3-iodobenzoate: generation of chiral crystals from achiral molecules. Acta Crystallographica Section C-Crystal Structure Communications. 2008; http://hdl.handle.net/11427/27668.en_ZA
dc.language.isoeng
dc.publisher.departmentDepartment of Chemistryen_ZA
dc.publisher.facultyFaculty of Scienceen_ZA
dc.publisher.institutionUniversity of Cape Town
dc.sourceActa Crystallographica Section C-Crystal Structure Communications
dc.source.urihttp://scripts.iucr.org/cgi-bin/paper?FG3065
dc.titleThe hydrogen-bonding patterns of 3-phenylpropylammonium benzoate and 3-phenylpropylammonium 3-iodobenzoate: generation of chiral crystals from achiral molecules
dc.typeJournal Article
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