Preparation and molecular structures of N′-(2-heteroarylmethylidene)-3-(3-pyridyl)acrylohydrazides

Karolina Jasiak , Agnieszka Kudelko , Katarzyna Gajda , Błażej Longin Dziuk , Bartosz Zarychta , Krzysztof Ejsmont

Abstract

The crystal and molecular structures of N′-(2-furylmethylidene)-3-(3-pyridyl)acrylohydrazide and N′-(2-thienylmethylidene)-3-(3-pyridyl)acrylohydrazide are reported, and the influence of the type of the heteroatom on the aromaticity of the aromatic rings is discussed. Both molecules are nearly planar. The geometry of the acrylohydrazide arrangement is comparable to that of homologous compounds. Density functional theory (DFT) calculations were performed in order to analyze the changes in the geometry of the studied compounds in the crystalline state and for the isolated molecule. The most significant changes were observed in the values of the N–N and C–N bond lengths. The harmonic oscillator model of aromaticity index, calculated for the furan and thiophene rings, demonstrated a noticeable increase in aromaticity in comparison to isolated rings and their DFT-calculated structures. By contrast, the nucleus independent chemical shift index indicated a decrease in aromatic character of the rings containing heteroatoms.
Author Karolina Jasiak - [Politechnika Śląska]
Karolina Jasiak,,
-
- Politechnika Śląska
, Agnieszka Kudelko - [Politechnika Śląska]
Agnieszka Kudelko,,
-
- Politechnika Śląska
, Katarzyna Gajda (FC)
Katarzyna Gajda,,
- Faculty of Chemistry
, Błażej Longin Dziuk (FC)
Błażej Longin Dziuk,,
- Faculty of Chemistry
, Bartosz Zarychta (FC)
Bartosz Zarychta,,
- Faculty of Chemistry
, Krzysztof Ejsmont (FC)
Krzysztof Ejsmont,,
- Faculty of Chemistry
Journal seriesZeitschrift Fur Naturforschung Section B = A Journal of Chemical Sciences, ISSN 0932-0776, e-ISSN 1865-7117, (A 15 pkt)
Issue year2018
Vol73
No10
Pages725-731
Publication size in sheets0.73
Keywords in Englishacroylhydrazides, aromaticity, crystal structure, density functional theory, heteroaryl substituents, quantum chemical calculations, X-ray structure determination
DOIDOI:10.1515/znb-2018-0132
URL https://www.degruyter.com/view/j/znb.2018.73.issue-10/znb-2018-0132/znb-2018-0132.xml
Languageen angielski
Score (nominal)15
ScoreMinisterial score = 15.0, 03-04-2019, ArticleFromJournal
Ministerial score (2013-2016) = 15.0, 03-04-2019, ArticleFromJournal
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