Stable Carbenes as Structural Components of Partially Saturated Sulfur-Containing Heterocycles

被引：1

作者：

Rozhenko, Alexander B. ^{[1
,2
]}

Horbenko, Yuliia S. ^{[1
,2
]}

Kyrylchuk, Andrii A. ^{[1
]}

Zarudnitskii, Evgenij V. ^{[1
]}

Mykhaylychenko, Sergiy S. ^{[1
]}

Shermolovich, Yuriy G. ^{[1
]}

Grafov, Andriy V. ^{[3
]}

机构：

[1] Natl Acad Sci, Inst Organ Chem, Murmanska Str 5, UA-02094 Kiev, Ukraine

[2] Natl Tech Univ Ukraine, Igor Sikorsky Kyiv Polytech Inst, Prosp Peremohy 37, UA-03056 Kiev, Ukraine

[3] Univ Helsinki, Dept Chem, AI Virtasen Aukio 1, Helsinki 00560, Finland

来源：

MOLECULES | 2022年 / 27卷 / 05期

关键词：

stable carbenes; ab initio calculations; thiadiazolines; bond elongation; AUXILIARY BASIS-SETS; DERIVATIVES; ACCURATE; CCSD(T); RI-MP2;

D O I：

10.3390/molecules27051458

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Recently, an unusual elongation of the C-S bond was observed experimentally for some sulfur-containing heterocycles. Using a superior ab initio (SCS-MP2/cc-pVTZ) level of theory, we showed that the phenomenon can be explained by a contribution of a donor-acceptor adduct of a carbene with an unsaturated ligand. One may achieve further elongation of the C-S bond, eventually turning it to a coordinate one, by increasing the stability of each part of the system as, e.g., in the utmost case of spiro adducts with Arduengo carbenes. The effect of carbene stability was quantified by employing the isodesmic reactions of carbene exchange.

引用

页数：9

共 14 条

[1] Xanthates routes to sulfur-containing heterocycles
Gholami, Fatemeh
Ansari, Shirin
Larijani, Bagher
Mahdavi, Mohammad
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2023, 992
[2] Iron-Catalyzed Synthesis of Sulfur-Containing Heterocycles
Bosset, Cyril
Lefebvre, Gauthier
Angibaud, Patrick
Stansfield, Ian
Meerpoel, Lieven
Berthelot, Didier
Guerinot, Amandine
Cossy, Janine
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (08) : 4020 - 4036
[3] Synthesis of sulfur-containing heterocycles via ring enlargement
Abdel-Wahab, Bakr F.
Shaaban, Saad
El-Hiti, Gamal A.
MOLECULAR DIVERSITY, 2018, 22 (02) : 517 - 542
[4] Synthesis of Sulfur-Containing Heterocycles by Electrophilic Addition Reactions of Disulfur Dichloride
Rakitin, Oleg A.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2020, 56 (07) : 837 - 847
[5] A formal [4+2] cycloaddition of sulfur-containing alkylidene heterocycles with allenic compounds
Docekal, Vojtech
Formanek, Bedrich
Cisarova, Ivana
Vesely, Jan
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (18) : 3259 - 3263
[6] Synthesis of Sulfur-Containing Heterocycles through Oxidative Carbon-Hydrogen Bond Functionalization
Cui, Yubo
Floreancig, Paul E.
ORGANIC LETTERS, 2012, 14 (07) : 1720 - 1723
[7] Synthesis, spectral and structural study of sulfur-containing copper(II) complexes
Metwally, M. A.
Farahat, Abdelbasset A.
Abdel-Wahab, Bakr F.
JOURNAL OF SULFUR CHEMISTRY, 2010, 31 (04) : 314 - 349
[8] Sulfur-containing heterocycles 14. New synthesis of cyclic anhydrides of 3-sulfinocarboxylic acids
Vasil'eva, T. P.
Shchetnikov, G. T.
Osipov, S. N.
RUSSIAN CHEMICAL BULLETIN, 2009, 58 (12) : 2494 - 2498
[9] Copper-Catalyzed Domino Synthesis of Sulfur-Containing Heterocycles Using Carbon Disulfide as a Building Block
Gan, Ziyu
Yan, Qiuli
Li, Guoqing
Li, Qin
Dou, Xiaomeng
Li, Guang-Yao
Yang, Daoshan
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (19) : 4558 - 4567
[10] Structural and Magnetic Investigation of Cobalt Valence Tautomeric Complexes with Sulfur-Containing Ligands
Wang, Ping
Yergeshbayeva, Sandugash
Lin, Xinsong
Bisht, Shubham
Gakiya-Teruya, Miguel
Shatruk, Michael
CRYSTAL GROWTH & DESIGN, 2023, 23 (04) : 2384 - 2394

← 1 2 →