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From a humorous post to a detailed quantum-chemical study: isocyanate synthesis revisited.
Beletsan, Oleg B; Gordiy, Igor; Lunkov, Sergey S; Kalinin, Mikhail A; Alkhimova, Larisa E; Nosach, Egor A; Ilin, Egor A; Bespalov, Alexandr V; Dallakyan, Olgert L; Chamkin, Aleksandr A; Prolomov, Ilya V; Zaripov, Radion A; Pershin, Andrey A; Protsenko, Bogdan O; Rusalev, Yury V; Oganov, Ruslan A; Kovaleva, Diana K; Mironov, Vladimir A; Dotsenko, Victor V; Genaev, Alexandr M; Sharapa, Dmitry I; Tikhonov, Denis S.
Afiliación
  • Beletsan OB; Department of Chemistry, Lomonosov Moscow State University, 119991 Moscow, Russia.
  • Gordiy I; ChemU Corporation Ltd, 17 17 Gr. Xenopoulou St., 3106 Limassol, Cyprus.
  • Lunkov SS; Department of Chemistry, Lomonosov Moscow State University, 119991 Moscow, Russia.
  • Kalinin MA; N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russia.
  • Alkhimova LE; Department of Chemistry, Lomonosov Moscow State University, 119991 Moscow, Russia.
  • Nosach EA; Center for Nature-Inspired Engineering, University of Tyumen, 625003 Tyumen, Russia.
  • Ilin EA; School of Natural Sciences, University of Tyumen, 625003 Tyumen, Russia.
  • Bespalov AV; Department of Fundamental Physical and Chemical Engineering, Lomonosov Moscow State University, 119234 Moscow, Russia.
  • Dallakyan OL; Department of Chemistry, Lomonosov Moscow State University, 119991 Moscow, Russia.
  • Chamkin AA; N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russia.
  • Prolomov IV; Department of Chemistry and High Technologies, Kuban State University, 149 Stavropolskaya St., 350040 Krasnodar, Russia.
  • Zaripov RA; Computational Material Science Laboratory, Department of Physics, Yerevan State University, 0025 Yerevan, Armenia.
  • Pershin AA; A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, 119334 Moscow, Russia.
  • Protsenko BO; D. Mendeleev University of Chemical Technology of Russia, 125047 Moscow, Russia.
  • Rusalev YV; N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russia.
  • Oganov RA; Skolkovo Institute of Science and Technology, 121205 Moscow, Russia.
  • Kovaleva DK; Samara Branch of Lebedev Physical Institute, 443011 Samara, Russia.
  • Mironov VA; Department of Physics, Samara University, 443086 Samara, Russia.
  • Dotsenko VV; The Smart Materials Research Institute, Southern Federal University, 344090 Rostov-on-Don, Russia.
  • Genaev AM; The Smart Materials Research Institute, Southern Federal University, 344090 Rostov-on-Don, Russia.
  • Sharapa DI; Department of Biochemistry, Lomonosov Moscow State University, 119991 Moscow, Russia.
  • Tikhonov DS; Department of Biochemistry, Lomonosov Moscow State University, 119991 Moscow, Russia.
Phys Chem Chem Phys ; 26(18): 13850-13861, 2024 May 08.
Article en En | MEDLINE | ID: mdl-38656824
ABSTRACT
Isocyanates play an essential role in modern manufacturing processes, especially in polyurethane production. There are numerous synthesis strategies for isocyanates both under industrial and laboratory conditions, which do not prevent searching for alternative highly efficient synthetic protocols. Here, we report a detailed theoretical investigation of the mechanism of sulfur dioxide-catalyzed rearrangement of phenylnitrile oxide into phenyl isocyanate, which was first reported in 1977. The DLPNO-CCSD(T) method and up-to-date DFT protocols were used to perform a highly accurate quantum-chemical study of the rearrangement mechanism. An overview of various organic and inorganic catalysts has revealed other potential catalysts, such as sulfur trioxide and selenium dioxide. Furthermore, the present study elucidated how substituents in phenylnitrile oxide influence reaction kinetics. This study was performed by a self-organized collaboration of scientists initiated by a humorous post on the VK social network.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Phys Chem Chem Phys Asunto de la revista: BIOFISICA / QUIMICA Año: 2024 Tipo del documento: Article País de afiliación: Rusia Pais de publicación: Reino Unido
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Phys Chem Chem Phys Asunto de la revista: BIOFISICA / QUIMICA Año: 2024 Tipo del documento: Article País de afiliación: Rusia Pais de publicación: Reino Unido