N-Tosyl-L-proline benzene hemisolvate: a rare example of a hydrogen-bonded carboxylic acid dimer with symmetrically disordered H atoms.

Autor: Wojnarska J; Faculty of Chemistry, Jagiellonian University, Gronostajowa 2, Krakow 30-387, Poland., Ostrowska K; Faculty of Chemistry, Jagiellonian University, Gronostajowa 2, Krakow 30-387, Poland., Gryl M; Faculty of Chemistry, Jagiellonian University, Gronostajowa 2, Krakow 30-387, Poland., Stadnicka KM; Faculty of Chemistry, Jagiellonian University, Gronostajowa 2, Krakow 30-387, Poland.
Jazyk: angličtina
Zdroj: Acta crystallographica. Section C, Structural chemistry [Acta Crystallogr C Struct Chem] 2019 Sep 01; Vol. 75 (Pt 9), pp. 1228-1233. Date of Electronic Publication: 2019 Aug 07.
DOI: 10.1107/S2053229619010829
Abstrakt: The carboxylic acid group is an example of a functional group which possess a good hydrogen-bond donor (-OH) and acceptor (C=O). For this reason, carboxylic acids have a tendency to self-assembly by the formation of hydrogen bonds between the donor and acceptor sites. We present here the crystal structure of N-tosyl-L-proline (TPOH) benzene hemisolvate {systematic name: (2S)-1-[(4-methylbenzene)sulfonyl]pyrrolidine-2-carboxylic acid benzene hemisolvate}, C 12 H 15 NO 4 S·0.5C 6 H 6 , (I), in which a cyclic R 2 2 (8) hydrogen-bonded carboxylic acid dimer with a strong O-(1/2H)...(1/2H)-O hydrogen bond is observed. The compound was characterized by single-crystal X-ray diffraction and NMR spectroscopy, and crystallizes in the space group I2 with half a benzene molecule and one TPOH molecule in the asymmetric unit. The H atom of the carboxyl OH group is disordered over a twofold axis. An analysis of the intermolecular interactions using the noncovalent interaction (NCI) index showed that the TPOH molecules form dimers due to the strong O-(1/2H)...(1/2H)-O hydrogen bond, while the packing of the benzene solvent molecules is governed by weak dispersive interactions. A search of the Cambridge Structural Database revealed that the disordered dimeric motif observed in (I) was found previously only in six crystal structures.
Databáze: MEDLINE
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