Self-association of diphenylpnictoginic acids in solution and solid state: covalent vs. hydrogen bonding

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Self-association of diphenylpnictoginic acids in solution and solid state: covalent vs. hydrogen bonding. / Yakubenko, Artyom A.; Puzyk, Aleksandra M.; Korostelev, Vladislav O.; Mulloyarova, Valeriia V.; Tupikina, Elena Yu ; Tolstoy, Peter M.; Antonov, Alexander S.

In: Physical Chemistry Chemical Physics, Vol. 24, No. 13, 15.03.2022, p. 7882-7892.

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

BibTeX

@article{422599c11d7747b8b0edcbcbf0a45213,

title = "Self-association of diphenylpnictoginic acids in solution and solid state: covalent vs. hydrogen bonding",

abstract = "Triphenylpnictogens were oxidized to access diphenylpnictioginic acids Ph2XOOH (X = P, As, Sb, Bi). It was shown that oxidation with chloramine-T does not lead to the cleavage of a C-pnictogen bond. The preliminary reductive cleavage with sodium in liquid ammonia followed by the oxidation with hydrogen peroxide was successfully utilised for the synthesis of diphenylphosphinic and diphenylarsinic acids. It was shown that in solid state (by means of XRD), all diphenylpnictoginic acids form polymeric chains. Diphenylbismuthinic and diphenylantimonic acids form polymeric covalent adducts, while diphenylphosphinic and diphenylarsinic chains are associated through hydrogen bonding. Unlike diphenylphosphinic acid, diphenilarsinic acid forms two polymorphs of hydrogen-bonded infinite chains. In solution in a polar aprotic solvent diphenylarsinic acid, similarly to dimethylarsinic, forms hydrogen-bonded cyclic dimers together with a small amount of cyclic trimers.",

keywords = "Hydrogen, Hydrogen Bonding, Polymers, Solvents",

author = "Yakubenko, {Artyom A.} and Puzyk, {Aleksandra M.} and Korostelev, {Vladislav O.} and Mulloyarova, {Valeriia V.} and Tupikina, {Elena Yu} and Tolstoy, {Peter M.} and Antonov, {Alexander S.}",

note = "Publisher Copyright: {\textcopyright} 2022 The Royal Society of Chemistry.",

year = "2022",

month = mar,

day = "15",

doi = "10.1039/d2cp00286h",

language = "English",

volume = "24",

pages = "7882--7892",

journal = "Physical Chemistry Chemical Physics",

issn = "1463-9076",

publisher = "Royal Society of Chemistry",

number = "13",

}

RIS

TY - JOUR

T1 - Self-association of diphenylpnictoginic acids in solution and solid state: covalent vs. hydrogen bonding

AU - Yakubenko, Artyom A.

AU - Puzyk, Aleksandra M.

AU - Korostelev, Vladislav O.

AU - Mulloyarova, Valeriia V.

AU - Tupikina, Elena Yu

AU - Tolstoy, Peter M.

AU - Antonov, Alexander S.

PY - 2022/3/15

Y1 - 2022/3/15

N2 - Triphenylpnictogens were oxidized to access diphenylpnictioginic acids Ph2XOOH (X = P, As, Sb, Bi). It was shown that oxidation with chloramine-T does not lead to the cleavage of a C-pnictogen bond. The preliminary reductive cleavage with sodium in liquid ammonia followed by the oxidation with hydrogen peroxide was successfully utilised for the synthesis of diphenylphosphinic and diphenylarsinic acids. It was shown that in solid state (by means of XRD), all diphenylpnictoginic acids form polymeric chains. Diphenylbismuthinic and diphenylantimonic acids form polymeric covalent adducts, while diphenylphosphinic and diphenylarsinic chains are associated through hydrogen bonding. Unlike diphenylphosphinic acid, diphenilarsinic acid forms two polymorphs of hydrogen-bonded infinite chains. In solution in a polar aprotic solvent diphenylarsinic acid, similarly to dimethylarsinic, forms hydrogen-bonded cyclic dimers together with a small amount of cyclic trimers.

AB - Triphenylpnictogens were oxidized to access diphenylpnictioginic acids Ph2XOOH (X = P, As, Sb, Bi). It was shown that oxidation with chloramine-T does not lead to the cleavage of a C-pnictogen bond. The preliminary reductive cleavage with sodium in liquid ammonia followed by the oxidation with hydrogen peroxide was successfully utilised for the synthesis of diphenylphosphinic and diphenylarsinic acids. It was shown that in solid state (by means of XRD), all diphenylpnictoginic acids form polymeric chains. Diphenylbismuthinic and diphenylantimonic acids form polymeric covalent adducts, while diphenylphosphinic and diphenylarsinic chains are associated through hydrogen bonding. Unlike diphenylphosphinic acid, diphenilarsinic acid forms two polymorphs of hydrogen-bonded infinite chains. In solution in a polar aprotic solvent diphenylarsinic acid, similarly to dimethylarsinic, forms hydrogen-bonded cyclic dimers together with a small amount of cyclic trimers.

KW - Hydrogen

KW - Hydrogen Bonding

KW - Polymers

KW - Solvents

UR - http://www.scopus.com/inward/record.url?scp=85127536539&partnerID=8YFLogxK

U2 - 10.1039/d2cp00286h

DO - 10.1039/d2cp00286h

M3 - Article

C2 - 35302575

AN - SCOPUS:85127536539

VL - 24

SP - 7882

EP - 7892

JO - Physical Chemistry Chemical Physics

JF - Physical Chemistry Chemical Physics

SN - 1463-9076

IS - 13

ER -

ID: 94028789