π–π Noncovalent Interaction Involving 1,2,4- and 1,3,4-Oxadiazole Systems: The Combined Experimental, Theoretical, and Database Study

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π–π Noncovalent Interaction Involving 1,2,4- and 1,3,4-Oxadiazole Systems: The Combined Experimental, Theoretical, and Database Study. / Baykov, Sergey V. ; Mikherdov, Alexander S. ; Novikov, Alexander S. ; Geyl , Kirill K. ; Tarasenko, Marina V. ; Gureev , Maxim A. ; Boyarskiy, Vadim P. .

In: Molecules, Vol. 26, No. 18, 5672, 18.09.2021.

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

BibTeX

@article{80df0591b62840a1a038715b265d7d0b,

title = "π–π Noncovalent Interaction Involving 1,2,4- and 1,3,4-Oxadiazole Systems: The Combined Experimental, Theoretical, and Database Study",

abstract = "A series of N-pyridyl ureas bearing 1,2,4- (1a, 2a, and 3a) and 1,3,4-oxadiazole moiety (1b, 2b, 3b) was prepared and characterized by HRMS, 1H and 13C NMR spectroscopy, as well as X-ray diffraction. The inspection of the crystal structures of (1–3)a,b and the Hirshfeld surface analysis made possible the recognition of the (oxadiazole)···(pyridine) and (oxadiazole)···(oxadiazole) interactions. The presence of these interactions was confirmed theoretically by DFT calculations, including NCI analysis for experimentally determined crystal structures as well as QTAIM analysis for optimized equilibrium structures. The preformed database survey allowed the verification of additional examples of relevant (oxadiazole)···π interactions both in Cambridge Structural Database and in Protein Data Bank, including the cocrystal of commercial anti-HIV drug Raltegravir.",

keywords = "noncovalent interactions, π···π interactions, oxadiazoles, X-ray diffraction studies, computational studies, databases search, Oxadiazoles, Databases search, Com-putational studies, Noncovalent interactions",

author = "Baykov, {Sergey V.} and Mikherdov, {Alexander S.} and Novikov, {Alexander S.} and Geyl, {Kirill K.} and Tarasenko, {Marina V.} and Gureev, {Maxim A.} and Boyarskiy, {Vadim P.}",

note = "Publisher Copyright: {\textcopyright} 2021 by the authors. Licensee MDPI, Basel, Switzerland.",

year = "2021",

month = sep,

day = "18",

doi = "10.3390/molecules26185672",

language = "English",

volume = "26",

journal = "Molecules",

issn = "1420-3049",

publisher = "MDPI AG",

number = "18",

}

RIS

TY - JOUR

T1 - π–π Noncovalent Interaction Involving 1,2,4- and 1,3,4-Oxadiazole Systems: The Combined Experimental, Theoretical, and Database Study

AU - Baykov, Sergey V.

AU - Mikherdov, Alexander S.

AU - Novikov, Alexander S.

AU - Geyl , Kirill K.

AU - Tarasenko, Marina V.

AU - Gureev , Maxim A.

AU - Boyarskiy, Vadim P.

PY - 2021/9/18

Y1 - 2021/9/18

N2 - A series of N-pyridyl ureas bearing 1,2,4- (1a, 2a, and 3a) and 1,3,4-oxadiazole moiety (1b, 2b, 3b) was prepared and characterized by HRMS, 1H and 13C NMR spectroscopy, as well as X-ray diffraction. The inspection of the crystal structures of (1–3)a,b and the Hirshfeld surface analysis made possible the recognition of the (oxadiazole)···(pyridine) and (oxadiazole)···(oxadiazole) interactions. The presence of these interactions was confirmed theoretically by DFT calculations, including NCI analysis for experimentally determined crystal structures as well as QTAIM analysis for optimized equilibrium structures. The preformed database survey allowed the verification of additional examples of relevant (oxadiazole)···π interactions both in Cambridge Structural Database and in Protein Data Bank, including the cocrystal of commercial anti-HIV drug Raltegravir.

AB - A series of N-pyridyl ureas bearing 1,2,4- (1a, 2a, and 3a) and 1,3,4-oxadiazole moiety (1b, 2b, 3b) was prepared and characterized by HRMS, 1H and 13C NMR spectroscopy, as well as X-ray diffraction. The inspection of the crystal structures of (1–3)a,b and the Hirshfeld surface analysis made possible the recognition of the (oxadiazole)···(pyridine) and (oxadiazole)···(oxadiazole) interactions. The presence of these interactions was confirmed theoretically by DFT calculations, including NCI analysis for experimentally determined crystal structures as well as QTAIM analysis for optimized equilibrium structures. The preformed database survey allowed the verification of additional examples of relevant (oxadiazole)···π interactions both in Cambridge Structural Database and in Protein Data Bank, including the cocrystal of commercial anti-HIV drug Raltegravir.

KW - noncovalent interactions

KW - π···π interactions

KW - oxadiazoles

KW - X-ray diffraction studies

KW - computational studies

KW - databases search

KW - Oxadiazoles

KW - Databases search

KW - Com-putational studies

KW - Noncovalent interactions

UR - https://www.mdpi.com/1420-3049/26/18/5672

UR - http://www.scopus.com/inward/record.url?scp=85115350775&partnerID=8YFLogxK

U2 - 10.3390/molecules26185672

DO - 10.3390/molecules26185672

M3 - Article

VL - 26

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 18

M1 - 5672

ER -

ID: 85821378