Selenium carboxylic acids betaine; 3,3′,3″-selenotris(propanoic acid) betaine, Se(CH2CH2COOH)2(CH2CH2COO)

Doudin, Khalid and Törnroos, Karl (2017). Selenium carboxylic acids betaine; 3,3′,3″-selenotris(propanoic acid) betaine, Se(CH2CH2COOH)2(CH2CH2COO). Journal of Molecular Structure, 1137 , 506–511.

Abstract

Attempts to prepare [Se(CH2CH2COOH)3]+Cl− from Se(CH2CH2COOH)2 and H2C=CHCOOH in concentrated hydrochloricacid, for the corresponding sulfonium salt, led exclusively to the Se-betaine,Se(CH2CH2COOH)2(CH2CH2COO). The Se-betaine crystallises in the space group P2l/c with the cell dimensions at 223 K, a = 5.5717(1), b = 24.6358(4), c = 8.4361(1) Å, β = 104.762(1)°, V = 1119.74(3) Å3, Z = 4, Dcalc = 1.763 Mgm− 3,μ = 3.364 Mm−1. The structure refined to RI = 0.0223 for 2801 reflections with F0 > 4σ(F0). In the crystalline state the molecule is intermolecularly linked to neighbouring molecules by a number of hydrogen bonds; a very strong carboxylic-carboxylate bond with an O⋯O distance of 2.4435(16) Å, a medium strong carboxylic-carboxylate bond with an O⋯O distance of 2.6431(16) Å and several weak O⋯H(CH2) with O⋯C distances between 3.2 and 3.3 Å. In the carboxylicgroup involved in the very strong hydrogen bond the O⋯H bond is antiperiplanar to the C O bond while the OH bond is periplanar to the C=O bond in the second carboxylic group. Based upon the C-O bond lengths and theelongation of the O-H bond involved in the strong hydrogen bond one may describe the compound as strongly linked units of Se(CH2CH2COOH)(CH2CH2COO)2 rather than Se(CH2CH2COOH)2(CH2CH2COO). The selenium atom forms two strong intramolecular 1,5-Se⋯O contacts, with a carboxylate oxygen atom, 2.9385(12) Å, and with a carboxylicoxygen atom, 2.8979(11) Å. To allow for these contacts the two organic fragments have been forced into the periplanar conformation. The molecule is only slightly asymmetric with regard to the C-Se-C bond angles but is very asymmetric with regard to the torsion angles.

Publication DOI: https://doi.org/10.1016/j.molstruc.2017.02.069
Divisions: Engineering & Applied Sciences > Chemical engineering & applied chemistry
Engineering & Applied Sciences > Polymer and advanced materials research group
Additional Information: © 2017, Elsevier. Licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/
Uncontrolled Keywords: Se-betaine,selenium betaine,selenium-oxygen intramolecular interactions,strong hydrogen bonding,crystal structures,77Se NMR,FTIR,Analytical Chemistry,Spectroscopy,Organic Chemistry,Inorganic Chemistry
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Related URLs: http://www.scop ... tnerID=8YFLogxK (Scopus URL)
Published Date: 2017-06-05
Authors: Doudin, Khalid ( 0000-0003-3604-9861)
Törnroos, Karl

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