2,2′,2″-Thiotris(acetic acid) betaine, S(CH 2 COOH) 2 (CH 2 COO), and 2,2′,2″-selenotris(acetic acid) betaine, Se(CH 2 COOH) 2 (CH 2 COO)


TThe title compounds, X(CH2COOH)2(CH2COO), X = S, 1, and X = Se, 2, have been characterised by FTIR, NMR and MS and by their crystal structures at 123(2) K. The FTIR spectra show two major peaks, at 1396 and 1731 cm−1 in 1 and at 1390 and 1721 cm−1 in 2. The 77Se NMR signal of 2 at 325.5 ppm is 83.4 ppm downfield from the signal of Se(CH2COOH)2 indicating a substantial selenonium character of 2. The two compounds are isostructural and have a pyramidal configuration. The C—X—C bond angles range from 99.29 to 103.14° in 1 and from 97.56 to 99.87° in 2. The Xsingle bondCsingle bondCdouble bond; length as m-dashO torsion angles for the three substituents are most different; one of the carboxylic acid groups attains the anti-conformation with rather short S⋯O(H) and Se⋯O(H) distances, 2.744 and 2.750 Å, the other acid group is synclinal and with longer S⋯Odouble bond; length as m-dashC and Se⋯Odouble bond; length as m-dashC distances, 3.063 and 3.090 Å, whereas the carboxylate group is in the Xsingle bondCsingle bondC plane with X⋯Osingle bondC distances of 2.869 and 2.908 Å in 1 and 2. The presence of these strong X⋯O interactions is suggested to be the cause for the very low Bronsted basicity of this class of betaines preventing salts of the corresponding acids, the presently unknown [X(CH2COOH)3]+ - cations, to be isolated. The molecules are linked together with two fairly strong but different hydrogen bonds to the carboxylate oxygen atoms with O⋯O distances of 2.493 and 2.580 Å in 1 and 2.489 and 2.581 Å in 2 and with one X⋯Odouble bond; length as m-dashC contact, 3.244 Å in 1 and 3.209 Å in 2. The carbonyl oxygen atoms do not participate significantly in intermolecular hydrogen bonding and there are no contacts between the heteroatoms.

Publication DOI: https://doi.org/10.1016/j.molstruc.2016.12.067
Divisions: College of Engineering & Physical Sciences > Aston Institute of Materials Research (AIMR)
College of Engineering & Physical Sciences > School of Infrastructure and Sustainable Engineering > Chemical Engineering & Applied Chemistry
Additional Information: © 2017, Elsevier. Licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ Supplementary data associated with this article can be found in the online version, at http://dx.doi.org/10.1016/j.molstruc.2016.12.067. These data include MOL files and InChiKeys of the most important compounds described in this article.
Uncontrolled Keywords: selenium betaine,sulphur betaine,77Se NMR,crystal structures,MS,FTIR,Analytical Chemistry,Spectroscopy,Organic Chemistry,Inorganic Chemistry
Publication ISSN: 0022-2860
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Related URLs: http://www.scop ... tnerID=8YFLogxK (Scopus URL)
PURE Output Type: Article
Published Date: 2017-04-15
Published Online Date: 2017-01-07
Accepted Date: 2016-12-22
Submitted Date: 2016-06-13
Authors: Doudin, Khalid (ORCID Profile 0000-0003-3604-9861)
Törnroos, Karl

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