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dc.contributor.author
Shabir, Ghulam
dc.contributor.author
Saeed, Aamer
dc.contributor.author
Qasim, Muhammad
dc.contributor.author
Bolte, Michael
dc.contributor.author
Hökelek, Tuncer
dc.contributor.author
Erben, Mauricio Federico
dc.date.available
2021-10-06T16:04:39Z
dc.date.issued
2020-08-17
dc.identifier.citation
Shabir, Ghulam; Saeed, Aamer; Qasim, Muhammad; Bolte, Michael; Hökelek, Tuncer; et al.; On the planarity of the cyclobutane ring in the crystal of dimethyl 2,4-bis(3,4-dimethoxyphenyl)cyclobutane-1,3-dicarboxylate: a natural bond orbital and Hirshfeld surface analysis study; Royal Society of Chemistry; New Journal of Chemistry; 44; 36; 17-8-2020; 15515-15525
dc.identifier.issn
1144-0546
dc.identifier.uri
http://hdl.handle.net/11336/142887
dc.description.abstract
Dimethyl 2,4-bis(3,4-dimethoxyphenyl)cyclobutane-1,3-dicarboxylate was synthesized by the dimerization of methyl 3-(3,4-dimethoxyphenyl)acrylate in methanol under photoirradiation by direct sunlight. Its molecular and crystal structures were determined by single crystal X-ray analysis. The molecule is located at the center of inversion. Thus, the asymmetric unit contains only one half of the molecule, and the central four-membered ring is in a slightly distorted square-planar arrangement. The residues on opposite sides of the four-membered ring are located on different faces of the ring, resembling the typical α-form for truxillic acid derivatives. The analysis of natural bond orbital population was performed and the effect of the σC-H → σC-H∗ hyperconjugative interactions is determined. In the crystal structure, the C-HMthcarbx⋯OCarbx and C-HMthoxy⋯OMthoxy [Mthcarbx = methylcarboxylate, Carbx = carboxylate and Mthoxy = methoxy] hydrogen bonds, enclosing R22(12) and R22(18) ring motifs, link the molecules into a three-dimensional architecture, in which they may be effective in the stabilization of the structure. The Hirshfeld surface analysis of the crystal structure confirms that the most important contributions for the crystal packing are from H⋯H (51.8%), H⋯O/O⋯H (31.5%) and H⋯C/C⋯H (15.3%) interactions. Hydrogen bonding and van der Waals interactions are dominant interactions in crystal packing.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Royal Society of Chemistry
dc.rights
info:eu-repo/semantics/restrictedAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
CYCLOBUTANE
dc.subject
CONFORMATION
dc.subject
STRUCTURE
dc.subject.classification
Química Inorgánica y Nuclear
dc.subject.classification
Ciencias Químicas
dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
dc.title
On the planarity of the cyclobutane ring in the crystal of dimethyl 2,4-bis(3,4-dimethoxyphenyl)cyclobutane-1,3-dicarboxylate: a natural bond orbital and Hirshfeld surface analysis study
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2021-08-20T19:55:16Z
dc.identifier.eissn
1369-9261
dc.journal.volume
44
dc.journal.number
36
dc.journal.pagination
15515-15525
dc.journal.pais
Reino Unido
dc.journal.ciudad
Cambridge
dc.description.fil
Fil: Shabir, Ghulam. Quaid-I-Azam University. Department of Chemistry; Pakistán
dc.description.fil
Fil: Saeed, Aamer. Quaid-I-Azam University. Department of Chemistry; Pakistán
dc.description.fil
Fil: Qasim, Muhammad. Quaid-I-Azam University. Department of Chemistry; Pakistán
dc.description.fil
Fil: Bolte, Michael. J. W. Goethe-Universität. Institut für Anorganische Chemie; Alemania
dc.description.fil
Fil: Hökelek, Tuncer. Hacettepe University. Department of Physics; Turquía
dc.description.fil
Fil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; Argentina
dc.journal.title
New Journal of Chemistry
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://xlink.rsc.org/?DOI=D0NJ02739A
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1039/D0NJ02739A
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