2,2′,2″-Thiotris(acetic acid) betaine, S(CH2COOH)2(CH2COO), and 2,2′,2″-selenotris(acetic acid) betaine, Se(CH2COOH)2(CH2COO)

Doudin, Khalid; Törnroos, Karl W.

doi:10.1016/j.molstruc.2016.12.067

Journal of Molecular Structure

2017

DOI: 10.1016/j.molstruc.2016.12.067

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2,2′,2″-Thiotris(acetic acid) betaine, S(CH2COOH)2(CH2COO), and 2,2′,2″-selenotris(acetic acid) betaine, Se(CH2COOH)2(CH2COO)

Khalid Doudin

Karl W. Törnroos

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Cited by 2 publications

References 24 publications

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Zero-, one-, two- and three-dimensional supramolecular architectures sustained by Se…O chalcogen bonding: A crystallographic survey

Tiekink

2021

Coordination Chemistry Reviews

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Highlights Selenium … oxygen chalcogen bonding is important in relevant crystal structures. Se … O interactions, operating alone, are found in 13% of possible structures. Se … O(carbonyl) interactions occur in 50% of possible structures. Zero-, one-, two- and three-dimensional architectures are sustained by Se … O interactions. One-dimensional chains are found in 55% of examples.

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Zero-, one-, two- and three-dimensional supramolecular architectures sustained by Se…O chalcogen bonding: A crystallographic survey

Tiekink

2021

Coordination Chemistry Reviews

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Selenium carboxylic acids betaine; 3,3′,3″-selenotris(propanoic acid) betaine, Se(CH 2 CH 2 COOH) 2 (CH 2 CH 2 COO)

Doudin

Törnroos

2017

Journal of Molecular Structure

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Attempts to prepare [Se(CH 2 CH 2 COOH) 3 ] + Clfrom Se(CH 2 CH 2 COOH) 2 and H 2 C=CHCOOH in concentrated hydrochloric acid, for the corresponding sulfonium salt, led exclusively to the Se-betaine, Se(CH 2 CH 2 COOH) 2 (CH 2 CH 2 COO). The Se-betaine crystallises in the space group P2 l /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) Å 3 , Z = 4, D calc = 1.763 Mgm-3 , µ = 3.364 Mm-1. The structure refined to R I = 0.0223 for 2801 reflections with F o > 4σ(F o). 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(CH 2) with O••••C distances between 3.2 and 3.3 Å. In the carboxylic group involved in the very strong hydrogen bond the O••••H bond is antiperiplanar to the C=O bond while the O-H bond is periplanar to the C=O bond in the second carboxylic group. Based upon the CO bond lengths and the elongation of the O-H bond involved in the strong hydrogen bond one may describe the compound as strongly linked units of Se(CH 2 CH 2 COOH)(CH 2 CH 2 COO) 2 rather than Se(CH 2 CH 2 COOH) 2 (CH 2 CH 2 COO). The selenium atom forms two strong intramolecular 1,5-Se••••O contacts, with a carboxylate oxygen atom, 2.9385(12) Å, and with a carboxylic oxygen 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.

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2,2′,2″-Thiotris(acetic acid) betaine, S(CH2COOH)2(CH2COO), and 2,2′,2″-selenotris(acetic acid) betaine, Se(CH2COOH)2(CH2COO)

Cited by 2 publications

References 24 publications

Zero-, one-, two- and three-dimensional supramolecular architectures sustained by Se…O chalcogen bonding: A crystallographic survey

Zero-, one-, two- and three-dimensional supramolecular architectures sustained by Se…O chalcogen bonding: A crystallographic survey

Selenium carboxylic acids betaine; 3,3′,3″-selenotris(propanoic acid) betaine, Se(CH 2 CH 2 COOH) 2 (CH 2 CH 2 COO)

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