2,5-Dibromothiophenes: halogen bond involving packing patterns and their relevance to solid-state polymerization

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2,5-Dibromothiophenes: halogen bond involving packing patterns and their relevance to solid-state polymerization. / Байков, Сергей Валентинович; Преснухина, София; Новиков, Александр Сергеевич; Шетнев, Антон; Боярский, Вадим Павлович ; Кукушкин, Вадим Юрьевич.

In: Crystal Growth and Design, Vol. 21, No. 4, 07.04.2021, p. 2526–2540.

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

BibTeX

@article{8d2209bcfb30484b8d5fd96c9824ab00,

title = "2,5-Dibromothiophenes: halogen bond involving packing patterns and their relevance to solid-state polymerization",

abstract = "A series of 2,5-dibromo-3-R-thiophenes (R = COONa 1, CN 2, CONH2 3, CON(H)Me 4, CON(H)Bn 5, CON(CH2CH2)2O 6, CON(H)NH2 7, CON(H)OH 8) were prepared and studied via high-resolution ESI-MS, 1H and 13C{H} NMR, IR, and X-ray diffraction. The analysis of the X-ray structures revealed Br···Br halogen bonds (XBs) as structure-directing interactions. A search of the Cambridge Structural Database showed an additional 12 structures of 2,5-dibromothiophenes whose structures featured Br···Br XBs. The crystal packing patterns for all these 2,5-dibromothiophenes were classified, and three general types were identified: (i) chains held by XBs, where each Br acts either as an XB donor or as an XB acceptor; (ii) zigzag arrays, where each Br functions simultaneously as an XB donor and acceptor; and (iii) rhombic assemblies with Br atoms at each vertex. DFT calculations, followed by topological analyses of the electron density distribution (QTAIM analysis) at the M06-2X/DZP-DKH level of theory, were performed to evaluate the strength of these XBs. The established energies were in the range from 0.5 to 2.2 kcal/mol, regardless of the packing type.",

keywords = "3,4-ETHYLENEDIOXYTHIOPHENE, ARYLATION, COMPLEXES, DERIVATIVES, ENERGY, NONCOVALENT INTERACTIONS, POLY(3,4-ETHYLENEDIOXYTHIOPHENE), POLYCONDENSATION, POLYTHIOPHENE, ZETA BASIS-SETS",

author = "Байков, {Сергей Валентинович} and София Преснухина and Новиков, {Александр Сергеевич} and Антон Шетнев and Боярский, {Вадим Павлович} and Кукушкин, {Вадим Юрьевич}",

note = "Publisher Copyright: {\textcopyright}",

year = "2021",

month = apr,

day = "7",

doi = "10.1021/acs.cgd.1c00184",

language = "English",

volume = "21",

pages = "2526–2540",

journal = "Crystal Growth and Design",

issn = "1528-7483",

publisher = "American Chemical Society",

number = "4",

}

RIS

TY - JOUR

T1 - 2,5-Dibromothiophenes: halogen bond involving packing patterns and their relevance to solid-state polymerization

AU - Байков, Сергей Валентинович

AU - Преснухина, София

AU - Новиков, Александр Сергеевич

AU - Шетнев, Антон

AU - Боярский, Вадим Павлович

AU - Кукушкин, Вадим Юрьевич

N1 - Publisher Copyright: ©

PY - 2021/4/7

Y1 - 2021/4/7

N2 - A series of 2,5-dibromo-3-R-thiophenes (R = COONa 1, CN 2, CONH2 3, CON(H)Me 4, CON(H)Bn 5, CON(CH2CH2)2O 6, CON(H)NH2 7, CON(H)OH 8) were prepared and studied via high-resolution ESI-MS, 1H and 13C{H} NMR, IR, and X-ray diffraction. The analysis of the X-ray structures revealed Br···Br halogen bonds (XBs) as structure-directing interactions. A search of the Cambridge Structural Database showed an additional 12 structures of 2,5-dibromothiophenes whose structures featured Br···Br XBs. The crystal packing patterns for all these 2,5-dibromothiophenes were classified, and three general types were identified: (i) chains held by XBs, where each Br acts either as an XB donor or as an XB acceptor; (ii) zigzag arrays, where each Br functions simultaneously as an XB donor and acceptor; and (iii) rhombic assemblies with Br atoms at each vertex. DFT calculations, followed by topological analyses of the electron density distribution (QTAIM analysis) at the M06-2X/DZP-DKH level of theory, were performed to evaluate the strength of these XBs. The established energies were in the range from 0.5 to 2.2 kcal/mol, regardless of the packing type.

AB - A series of 2,5-dibromo-3-R-thiophenes (R = COONa 1, CN 2, CONH2 3, CON(H)Me 4, CON(H)Bn 5, CON(CH2CH2)2O 6, CON(H)NH2 7, CON(H)OH 8) were prepared and studied via high-resolution ESI-MS, 1H and 13C{H} NMR, IR, and X-ray diffraction. The analysis of the X-ray structures revealed Br···Br halogen bonds (XBs) as structure-directing interactions. A search of the Cambridge Structural Database showed an additional 12 structures of 2,5-dibromothiophenes whose structures featured Br···Br XBs. The crystal packing patterns for all these 2,5-dibromothiophenes were classified, and three general types were identified: (i) chains held by XBs, where each Br acts either as an XB donor or as an XB acceptor; (ii) zigzag arrays, where each Br functions simultaneously as an XB donor and acceptor; and (iii) rhombic assemblies with Br atoms at each vertex. DFT calculations, followed by topological analyses of the electron density distribution (QTAIM analysis) at the M06-2X/DZP-DKH level of theory, were performed to evaluate the strength of these XBs. The established energies were in the range from 0.5 to 2.2 kcal/mol, regardless of the packing type.

KW - 3,4-ETHYLENEDIOXYTHIOPHENE

KW - ARYLATION

KW - COMPLEXES

KW - DERIVATIVES

KW - ENERGY

KW - NONCOVALENT INTERACTIONS

KW - POLY(3,4-ETHYLENEDIOXYTHIOPHENE)

KW - POLYCONDENSATION

KW - POLYTHIOPHENE

KW - ZETA BASIS-SETS

UR - http://www.scopus.com/inward/record.url?scp=85104948242&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/de3e502a-71d6-351f-8867-bf99fc33e7fb/

U2 - 10.1021/acs.cgd.1c00184

DO - 10.1021/acs.cgd.1c00184

M3 - Article

VL - 21

SP - 2526

EP - 2540

JO - Crystal Growth and Design

JF - Crystal Growth and Design

SN - 1528-7483

IS - 4

ER -

ID: 76378409