Dualism of 1,2,4-Oxadiazole Ring in Noncovalent Interactions with Carboxylic Group

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Dualism of 1,2,4-Oxadiazole Ring in Noncovalent Interactions with Carboxylic Group. / Baykov, Sergey V. ; Tarasenko, Marina V. ; Semenov, Artem V. ; Katlenok, Evgeniy A. ; Shetnev, Anton A. ; Boyarskiy, Vadim P. .

In: Journal of Molecular Structure, Vol. 1262, 132974, 15.08.2022.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{cc50ccc6f53c40bb81ba7b24b78f6ecf,

title = "Dualism of 1,2,4-Oxadiazole Ring in Noncovalent Interactions with Carboxylic Group",

abstract = "A number of cyclohexane and cyclohexene carboxylic acids bearing 1,2,4-oxadiazole substituent were prepared via condensation of amidoximes with anhydrides of corresponding dicarboxylic acids. All prepared compounds were studied via HRMS, 1H and 13C NMR. In addition, for five acids crystalline structures were obtained via X-ray diffraction analysis. Inspection of these X-ray structures revealed two type previously undescribed noncovalent interactions between oxadiazole ring and carboxylic group: O(carboxyl)•••C(oxadiazole) and O(oxadiazole)•••C(carboxyl).Computational investigation by a number of theoretical approaches (the quantum theory of atoms in molecules, the independent gradient model, natural bond orbital, molecular electrostatic potential, and Kohn-Sham energy decomposition analyses, as well as the domain based local pair-natural orbital coupled-cluster and atomic-dipole-moment-corrected Hirshfeld methods) demonstrated that these interactions are caused by the packing effect and have an electrostatic and dispersive nature.",

keywords = "oxadiazoles, noncovalent interactions, XRD, DFT, QTAIM, IGMH, Oxadiazoles, QTAIM, IGMH, Noncovalent interactions",

author = "Baykov, {Sergey V.} and Tarasenko, {Marina V.} and Semenov, {Artem V.} and Katlenok, {Evgeniy A.} and Shetnev, {Anton A.} and Boyarskiy, {Vadim P.}",

note = "Publisher Copyright: {\textcopyright} 2022 Elsevier B.V.",

year = "2022",

month = aug,

day = "15",

doi = "10.1016/j.molstruc.2022.132974",

language = "English",

volume = "1262",

journal = "Journal of Molecular Structure",

issn = "0022-2860",

publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Dualism of 1,2,4-Oxadiazole Ring in Noncovalent Interactions with Carboxylic Group

AU - Baykov, Sergey V.

AU - Tarasenko, Marina V.

AU - Semenov, Artem V.

AU - Katlenok, Evgeniy A.

AU - Shetnev, Anton A.

AU - Boyarskiy, Vadim P.

PY - 2022/8/15

Y1 - 2022/8/15

N2 - A number of cyclohexane and cyclohexene carboxylic acids bearing 1,2,4-oxadiazole substituent were prepared via condensation of amidoximes with anhydrides of corresponding dicarboxylic acids. All prepared compounds were studied via HRMS, 1H and 13C NMR. In addition, for five acids crystalline structures were obtained via X-ray diffraction analysis. Inspection of these X-ray structures revealed two type previously undescribed noncovalent interactions between oxadiazole ring and carboxylic group: O(carboxyl)•••C(oxadiazole) and O(oxadiazole)•••C(carboxyl).Computational investigation by a number of theoretical approaches (the quantum theory of atoms in molecules, the independent gradient model, natural bond orbital, molecular electrostatic potential, and Kohn-Sham energy decomposition analyses, as well as the domain based local pair-natural orbital coupled-cluster and atomic-dipole-moment-corrected Hirshfeld methods) demonstrated that these interactions are caused by the packing effect and have an electrostatic and dispersive nature.

AB - A number of cyclohexane and cyclohexene carboxylic acids bearing 1,2,4-oxadiazole substituent were prepared via condensation of amidoximes with anhydrides of corresponding dicarboxylic acids. All prepared compounds were studied via HRMS, 1H and 13C NMR. In addition, for five acids crystalline structures were obtained via X-ray diffraction analysis. Inspection of these X-ray structures revealed two type previously undescribed noncovalent interactions between oxadiazole ring and carboxylic group: O(carboxyl)•••C(oxadiazole) and O(oxadiazole)•••C(carboxyl).Computational investigation by a number of theoretical approaches (the quantum theory of atoms in molecules, the independent gradient model, natural bond orbital, molecular electrostatic potential, and Kohn-Sham energy decomposition analyses, as well as the domain based local pair-natural orbital coupled-cluster and atomic-dipole-moment-corrected Hirshfeld methods) demonstrated that these interactions are caused by the packing effect and have an electrostatic and dispersive nature.

KW - oxadiazoles

KW - noncovalent interactions

KW - XRD

KW - DFT

KW - QTAIM

KW - IGMH

KW - Oxadiazoles

KW - QTAIM, IGMH

KW - Noncovalent interactions

UR - https://linkinghub.elsevier.com/retrieve/pii/S0022286022006433

UR - https://www.mendeley.com/catalogue/035a4dc7-f134-3902-9557-2f03cac50573/

UR - http://www.scopus.com/inward/record.url?scp=85127762148&partnerID=8YFLogxK

U2 - 10.1016/j.molstruc.2022.132974

DO - 10.1016/j.molstruc.2022.132974

M3 - Article

VL - 1262

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

SN - 0022-2860

M1 - 132974

ER -

ID: 93917869