Noncovalent Sulfoxide−Nitrile Coupling Involving Four-Center Heteroleptic Dipole−Dipole Interactions between the Sulfinyl and Nitrile Groups

Standard

Noncovalent Sulfoxide−Nitrile Coupling Involving Four-Center Heteroleptic Dipole−Dipole Interactions between the Sulfinyl and Nitrile Groups. / Ivanov, Daniil M. ; Baykov, Sergey V. ; Novikov, Alexander S. ; Romanenko, Galina ; Bokach, Nadezhda A. ; Evarestov, Robert A. ; Kukushkin, Vadim Yu. .

в: Crystal Growth and Design, Том 20, № 5, 06.05.2020, стр. 3417-3428.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

BibTeX

@article{9b26f6ab230e450b8b0342a612500742,

title = "Noncovalent Sulfoxide−Nitrile Coupling Involving Four-Center Heteroleptic Dipole−Dipole Interactions between the Sulfinyl and Nitrile Groups",

abstract = "The 4-X-5-nitro substituted phthalodinitriles (X = Br 1, I 2) were crystallized from Me 2SO solutions affording crystalline adducts (1-2)·Me 2SO, which were characterized by X-ray crystallography at various temperatures (>40 K). The two adducts are isomorphic and exhibit in their XRD structures the heteroleptic dipole-dipole four-center contacts between the S=O and CN functionalities. Results of DFT calculations within the {"}molecular{"} approach based on the experimental X-ray geometries of (1-2)·Me 2SO followed by the topological analysis of the electron density distribution (QTAIM analysis) at the M06-2X/x2c-TZVPPall level of theory confirm the presence of sulfoxide-nitrile heteroleptic dipole-dipole interactions in the solid state (their estimated strength does not exceed 7 kcal/mol). DFT calculations for 1·Me 2SO were also performed in both the periodic and {"}molecular{"} models at the DFT M06 level of theory using DZVP and pob-TZVP bases; the results of the electron density topological analysis are similar in both models. ",

keywords = "HYDROGEN-BOND, DIMETHYL-SULFOXIDE, CRYSTAL-STRUCTURES, HALOGEN, SOLVENT, ASSOCIATION, ACETONITRILE, COMPLEXES, WATER, PI",

author = "Ivanov, {Daniil M.} and Baykov, {Sergey V.} and Novikov, {Alexander S.} and Galina Romanenko and Bokach, {Nadezhda A.} and Evarestov, {Robert A.} and Kukushkin, {Vadim Yu.}",

note = "Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = may,

day = "6",

doi = "10.1021/acs.cgd.0c00196",

language = "English",

volume = "20",

pages = "3417--3428",

journal = "Crystal Growth and Design",

issn = "1528-7483",

publisher = "American Chemical Society",

number = "5",

}

RIS

TY - JOUR

T1 - Noncovalent Sulfoxide−Nitrile Coupling Involving Four-Center Heteroleptic Dipole−Dipole Interactions between the Sulfinyl and Nitrile Groups

AU - Ivanov, Daniil M.

AU - Baykov, Sergey V.

AU - Novikov, Alexander S.

AU - Romanenko, Galina

AU - Bokach, Nadezhda A.

AU - Evarestov, Robert A.

AU - Kukushkin, Vadim Yu.

PY - 2020/5/6

Y1 - 2020/5/6

N2 - The 4-X-5-nitro substituted phthalodinitriles (X = Br 1, I 2) were crystallized from Me 2SO solutions affording crystalline adducts (1-2)·Me 2SO, which were characterized by X-ray crystallography at various temperatures (>40 K). The two adducts are isomorphic and exhibit in their XRD structures the heteroleptic dipole-dipole four-center contacts between the S=O and CN functionalities. Results of DFT calculations within the "molecular" approach based on the experimental X-ray geometries of (1-2)·Me 2SO followed by the topological analysis of the electron density distribution (QTAIM analysis) at the M06-2X/x2c-TZVPPall level of theory confirm the presence of sulfoxide-nitrile heteroleptic dipole-dipole interactions in the solid state (their estimated strength does not exceed 7 kcal/mol). DFT calculations for 1·Me 2SO were also performed in both the periodic and "molecular" models at the DFT M06 level of theory using DZVP and pob-TZVP bases; the results of the electron density topological analysis are similar in both models.

AB - The 4-X-5-nitro substituted phthalodinitriles (X = Br 1, I 2) were crystallized from Me 2SO solutions affording crystalline adducts (1-2)·Me 2SO, which were characterized by X-ray crystallography at various temperatures (>40 K). The two adducts are isomorphic and exhibit in their XRD structures the heteroleptic dipole-dipole four-center contacts between the S=O and CN functionalities. Results of DFT calculations within the "molecular" approach based on the experimental X-ray geometries of (1-2)·Me 2SO followed by the topological analysis of the electron density distribution (QTAIM analysis) at the M06-2X/x2c-TZVPPall level of theory confirm the presence of sulfoxide-nitrile heteroleptic dipole-dipole interactions in the solid state (their estimated strength does not exceed 7 kcal/mol). DFT calculations for 1·Me 2SO were also performed in both the periodic and "molecular" models at the DFT M06 level of theory using DZVP and pob-TZVP bases; the results of the electron density topological analysis are similar in both models.

KW - HYDROGEN-BOND

KW - DIMETHYL-SULFOXIDE

KW - CRYSTAL-STRUCTURES

KW - HALOGEN

KW - SOLVENT

KW - ASSOCIATION

KW - ACETONITRILE

KW - COMPLEXES

KW - WATER

KW - PI

UR - http://www.scopus.com/inward/record.url?scp=85085151539&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/f4ca4a21-44c5-3291-9b5f-1ced5d172d09/

U2 - 10.1021/acs.cgd.0c00196

DO - 10.1021/acs.cgd.0c00196

M3 - Article

VL - 20

SP - 3417

EP - 3428

JO - Crystal Growth and Design

JF - Crystal Growth and Design

SN - 1528-7483

IS - 5

ER -

ID: 53561637