About: On constitutional isomers and tautomers of oxadiazolones and their mono- and disulfur analogues (C(2)H(2)N(2)XY; X, Y = S, O)

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About: On constitutional isomers and tautomers of oxadiazolones and their mono- and disulfur analogues (C(2)H(2)N(2)XY; X, Y = S, O) Goto Sponge NotDistinct Permalink

An Entity of Type : schema:ScholarlyArticle, within Data Space : covidontheweb.inria.fr associated with source document(s)

Attributes	Values
type	Academic Article research paper schema:ScholarlyArticle
isDefinedBy	Covid-on-the-Web dataset
title	On constitutional isomers and tautomers of oxadiazolones and their mono- and disulfur analogues (C(2)H(2)N(2)XY; X, Y = S, O)
Creator	Dobrowolski, Jan Zyna Karpiń Ska, Gra
source	Elsevier; Medline; PMC
abstract	The constitutional isomers and tautomers of oxadiazolones, as well as their mono- and disulfur analogues, were calculated at the B3LYP/aug-cc-pVDZ level. Four groups of 30 molecules each were considered: oxadiazolone, oxadiazolthione, thiadiazolone, and thiadiazolthione isomers. The compounds were categorized into six groups according to permutations of three heteroatoms in the five-membered ring. Additionally, each of the constitutional isomer was considered to have five tautomers conserving stable five-membered ring: two NH tautomers, two rotameric OH (or SH) forms and one CH(2) tautomer. It appeared that the largest difference between oxadiazolone O and S analogues is produced by the kind of chalcogen atom in the ring, which is strained when the O atom is in the ring while much less strained when the S-atom, of much larger van der Waals radius, is built into the ring. The external chalcogen is only modifying the general energetic factors. The comparison of energetics of analogous groups of molecules with thiadiazole and oxadiazole rings is done in details as well as differences resulting from different external chalcogen atoms are discussed as well. The presence of water surrounding was mimicked with the IEF-PCM implicit water model which did not change general isomer relative stability picture, but for some special cases indicated an extra stability of the forms with external OH or SH groups. The aromaticity monitored by the structural HOMA aromaticity index shows that the systems are not additionally stabilized by pi-electron delocalization. The fair linear correlation between the aromaticity indices of oxadiazolones and oxadiazolthiones shows that the pi-electron system in the studied systems is not sensitive to change of the external chalcogen group.
has issue date	2013-02-01(xsd:dateTime)
bibo:doi	10.1016/j.comptc.2012.11.003
bibo:pmid	32288988
has license	no-cc
sha1sum (hex)	811ae9afd7a07d05da065433fcccafda4ca8ca33
schema:url	https://doi.org/10.1016/j.comptc.2012.11.003
resource representing a document's title	On constitutional isomers and tautomers of oxadiazolones and their mono- and disulfur analogues (C(2)H(2)N(2)XY; X, Y = S, O)
has PubMed Central identifier	PMC7104208
has PubMed identifier	32288988
schema:publication	Comput Theor Chem
resource representing a document's body	covid:811ae9afd7a07d05da065433fcccafda4ca8ca33#body_text
is schema:about of	named entity 'MONO' named entity 'INDICATED' named entity 'STRAINED' named entity 'CONSTITUTIONAL ISOMERS' named entity 'EXTRA' named entity 'AROMATICITY' named entity 'KIND' named entity 'SENSITIVE TO' named entity 'RELATIVE' named entity 'CONSTITUTIONAL' named entity 'DETAILS' named entity 'INDICES' named entity 'MONITORED' named entity 'STRUCTURAL' named entity 'BUT' named entity 'CASES' named entity 'CHANGE' named entity 'OXADIAZOLE' named entity 'PRESENCE OF' named entity 'ISOMERS' named entity 'DISULFUR' named entity 'FAIR' named entity 'ATOMS' named entity 'PICTURE' named entity 'CALCULATED' named entity 'STABLE' named entity 'LEVEL' named entity 'COMPARISON' named entity 'CONSTITUTIONAL ISOMERS' named entity 'SYSTEMS' named entity 'FORMS' named entity 'RING' named entity 'TO CHANGE' named entity 'MOLECULES' named entity 'RESULTING FROM' named entity 'THIADIAZOLE' named entity 'MUCH' named entity 'SYSTEM' named entity 'LINEAR' named entity 'THEIR' named entity 'MODEL' named entity 'TAUTOMER' named entity 'SURROUNDING' named entity 'WATER' named entity 'ENERGETIC' named entity 'ISOMER' named entity 'HOMA' named entity 'GROUPS' named entity 'HAVE' named entity 'SPECIAL' named entity 'ACCORDING' named entity 'MODIFYING' named entity 'VAN DER WAALS RADIUS' named entity 'DISULFUR' named entity 'CONSIDERED' named entity 'PCM' named entity 'H 2' named entity 'CHALCOGEN' named entity 'MONO' named entity 'DIFFERENCE' named entity 'IEF' named entity 'GROUP' named entity 'LARGEST' named entity 'CATEGORIZED' named entity 'ATOM' named entity 'ELECTRON' named entity 'EXTERNAL' named entity 'STABILITY' named entity 'CORRELATION' named entity 'LARGER' named entity 'DID' named entity 'GENERAL' named entity 'RINGS' named entity 'INDEX' named entity 'STABILIZED' named entity 'DIFFERENT' named entity 'THEIR' covid:arg/811ae9afd7a07d05da065433fcccafda4ca8ca33 named entity 'tautomer' named entity 'pi-electron'

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