Synthesis, conformation and Hirshfeld surface analysis of benzoxazole methyl ester as a versatile building block for heterocycles

Mostrar todas las versiones(2)

Solventless cyclocondensation of 2-aminothiophenol with thiourea afforded the benzo[d]oxazole-2-thiol (3a) capable of existing also in the tautomeric form benzo[d]oxazole-2(3H)-thione (3b). Acylation with methyl chloroacetate in dry ethanol in absence of any base or catalyst selectively afforded the...

Descripción completa

Detalles Bibliográficos
Autores principales: Saeed, Aamer, Shabir, Ghulam, Hökelek, Tuncer, Flörke, Ulrich, Erben, Mauricio Federico
Formato: Articulo
Lenguaje:Inglés
Publicado: 2021
Materias:
Ciencias Exactas
Química
Molecular structure
benzo[d]oxazole-2(3H)-thione
Hirshfeld surface analysis
Natural bond orbital
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/131982
Aporte de:
SEDICI (UNLP) de Universidad Nacional de La Plata
id I19-R120-10915-131982
record_format dspace
institution Universidad Nacional de La Plata
institution_str I-19
repository_str R-120
collection SEDICI (UNLP)
language Inglés
topic Ciencias Exactas
Química
Molecular structure
benzo[d]oxazole-2(3H)-thione
Hirshfeld surface analysis
Natural bond orbital
spellingShingle Ciencias Exactas
Química
Molecular structure
benzo[d]oxazole-2(3H)-thione
Hirshfeld surface analysis
Natural bond orbital
Saeed, Aamer
Shabir, Ghulam
Hökelek, Tuncer
Flörke, Ulrich
Erben, Mauricio Federico
Synthesis, conformation and Hirshfeld surface analysis of benzoxazole methyl ester as a versatile building block for heterocycles
topic_facet Ciencias Exactas
Química
Molecular structure
benzo[d]oxazole-2(3H)-thione
Hirshfeld surface analysis
Natural bond orbital
description Solventless cyclocondensation of 2-aminothiophenol with thiourea afforded the benzo[d]oxazole-2-thiol (3a) capable of existing also in the tautomeric form benzo[d]oxazole-2(3H)-thione (3b). Acylation with methyl chloroacetate in dry ethanol in absence of any base or catalyst selectively afforded the S-substituted ester 2-(methoxycarbonylmethylthio)benzo[d]oxazole (4a) in preference to the corresponding N-substituted ester N-(methoxycarbonylmethyl)thioxobenzoxazole (4b). Quantum chemical calculations were conducted to determine the conformational landscape and NBO population analysis showed the strong electronic delocalization via resonance interactions on the 2-mercaptobenzaxazole group. The anomeric effect and the occurrence of a 1,4-S···O intramolecular interactions suggest the relevance of chalcogen bonding in the conformational preference. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H···H (33.2%), H···O/O···H (19.9%) and H···C/C···H (17.8%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, the C-H···O hydrogen-bond energy is 44.8 kJ mol-1.
format Articulo
Articulo
author Saeed, Aamer
Shabir, Ghulam
Hökelek, Tuncer
Flörke, Ulrich
Erben, Mauricio Federico
author_facet Saeed, Aamer
Shabir, Ghulam
Hökelek, Tuncer
Flörke, Ulrich
Erben, Mauricio Federico
author_sort Saeed, Aamer
title Synthesis, conformation and Hirshfeld surface analysis of benzoxazole methyl ester as a versatile building block for heterocycles
title_short Synthesis, conformation and Hirshfeld surface analysis of benzoxazole methyl ester as a versatile building block for heterocycles
title_full Synthesis, conformation and Hirshfeld surface analysis of benzoxazole methyl ester as a versatile building block for heterocycles
title_fullStr Synthesis, conformation and Hirshfeld surface analysis of benzoxazole methyl ester as a versatile building block for heterocycles
title_full_unstemmed Synthesis, conformation and Hirshfeld surface analysis of benzoxazole methyl ester as a versatile building block for heterocycles
title_sort synthesis, conformation and hirshfeld surface analysis of benzoxazole methyl ester as a versatile building block for heterocycles
publishDate 2021
url http://sedici.unlp.edu.ar/handle/10915/131982
work_keys_str_mv AT saeedaamer synthesisconformationandhirshfeldsurfaceanalysisofbenzoxazolemethylesterasaversatilebuildingblockforheterocycles
AT shabirghulam synthesisconformationandhirshfeldsurfaceanalysisofbenzoxazolemethylesterasaversatilebuildingblockforheterocycles
AT hokelektuncer synthesisconformationandhirshfeldsurfaceanalysisofbenzoxazolemethylesterasaversatilebuildingblockforheterocycles
AT florkeulrich synthesisconformationandhirshfeldsurfaceanalysisofbenzoxazolemethylesterasaversatilebuildingblockforheterocycles
AT erbenmauriciofederico synthesisconformationandhirshfeldsurfaceanalysisofbenzoxazolemethylesterasaversatilebuildingblockforheterocycles
bdutipo_str Repositorios
_version_ 1764820453755453440

Ejemplares similares