DVOŘÁKOVÁ, Hana, Jan LANG, Jiří VLACH, Jan SÝKORA, Michal ČAJAN, Michal HIML, Michaela POJAROVÁ, Ivan STIBOR a Pavel LHOTÁK. Partially O-Alkylated thiacalix[4]arenes: Synthesis, molecular and crystal structures, conformational behavior. Journal of Organic Chemistry. Columbus, OH, USA: the American Chemical Society, 2007, roč. 72, č. 19, s. 7157-7166. ISSN 0022-3263.
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Základní údaje
Originální název Partially O-Alkylated thiacalix[4]arenes: Synthesis, molecular and crystal structures, conformational behavior
Název česky Parciálně O-alkylované thiacalix[4]areny: Syntéza, molekulové a krystalové struktury, konformační chování
Autoři DVOŘÁKOVÁ, Hana (203 Česká republika, garant), Jan LANG (203 Česká republika), Jiří VLACH (203 Česká republika), Jan SÝKORA (203 Česká republika), Michal ČAJAN (203 Česká republika), Michal HIML (203 Česká republika), Michaela POJAROVÁ (203 Česká republika), Ivan STIBOR (203 Česká republika) a Pavel LHOTÁK (203 Česká republika).
Vydání Journal of Organic Chemistry, Columbus, OH, USA, the American Chemical Society, 2007, 0022-3263.
Další údaje
Originální jazyk angličtina
Typ výsledku Článek v odborném periodiku
Obor 10401 Organic chemistry
Stát vydavatele Spojené státy
Utajení není předmětem státního či obchodního tajemství
Impakt faktor Impact factor: 3.959
Kód RIV RIV/00216224:14310/07:00019544
Organizační jednotka Přírodovědecká fakulta
UT WoS 000249371200010
Klíčová slova anglicky ALTERNATE CONFORMATION; CONE INTERCONVERSION; INFINITE CHANNELS; SOLID-STATE; X-RAY; COMPLEXATION; THIACALIXARENES; CONFORMERS; H-1-NMR; NMR
Štítky ALTERNATE CONFORMATION, Complexation, CONE INTERCONVERSION, CONFORMERS, H-1-NMR, INFINITE CHANNELS, NMR, SOLID-STATE, THIACALIXARENES, x-ray
Příznaky Recenzováno
Změnil Změnil: doc. RNDr. Michal Čajan, Ph.D., učo 6989. Změněno: 7. 1. 2008 09:37.
Anotace
NMR spectroscopy, X-ray diffraction analysis, and quantum chemical calculations were used for conformational behavior study of partially alkylated thiacalix[4]arenes bearing methyl (1), ethyl (2), or propyl (3) groups at the lower rim. The conformational properties are governed by two basic effects: (i) stabilization by intramolecular hydrogen bonds, and (ii) sterical requirements of the alkoxy groups at the lower rim. While the monosubstituted derivatives la and 3a adopt the cone conformation in solution, distally disubstituted compounds 1b, 1'b, 2b, 2'b, 3b, and 3'b exhibit several. interesting conformational features. They prefer pinched cone conformation in solution, and, except for 3'b, they form also 1,2-alternate conformation, which is flexible and undergoes rather fast transition between two identical structures. The crystal structures of the compounds 1b, 2b, 2'b, and 3b revealed yet quite rare 1,2-alternate conformation forming molecular channels held together by pi-pi interactions. Different channels-with hexagonal symmetry, 0.26 nm wide-are formed in the crystal structure of the pinched cone conformation of 3b. An uncommon hydrogen bonding pattern was found in dimethoxy and dipropoxy derivatives 1'b and 3'b that adopt distorted cone conformations in crystal. Trialkoxy-substituted compounds 1c and 3c adopt the partial cone conformation in solution. A higher mobility of methyl derivative 1c enables also existence of the cone conformer.
Anotace česky
NMR spectroscopy, X-ray diffraction analysis, and quantum chemical calculations were used for conformational behavior study of partially alkylated thiacalix[4]arenes bearing methyl (1), ethyl (2), or propyl (3) groups at the lower rim. The conformational properties are governed by two basic effects: (i) stabilization by intramolecular hydrogen bonds, and (ii) sterical requirements of the alkoxy groups at the lower rim. While the monosubstituted derivatives la and 3a adopt the cone conformation in solution, distally disubstituted compounds 1b, 1'b, 2b, 2'b, 3b, and 3'b exhibit several. interesting conformational features. They prefer pinched cone conformation in solution, and, except for 3'b, they form also 1,2-alternate conformation, which is flexible and undergoes rather fast transition between two identical structures. The crystal structures of the compounds 1b, 2b, 2'b, and 3b revealed yet quite rare 1,2-alternate conformation forming molecular channels held together by pi-pi interactions. Different channels-with hexagonal symmetry, 0.26 nm wide-are formed in the crystal structure of the pinched cone conformation of 3b. An uncommon hydrogen bonding pattern was found in dimethoxy and dipropoxy derivatives 1'b and 3'b that adopt distorted cone conformations in crystal. Trialkoxy-substituted compounds 1c and 3c adopt the partial cone conformation in solution. A higher mobility of methyl derivative 1c enables also existence of the cone conformer.
Návaznosti
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Investor: Akademie věd ČR, Léčiva na bázi sacharidů a calixarenů – design, struktura, protinádorová a protivirová aktivita
MSM0021622413, záměrNázev: Proteiny v metabolismu a při interakci organismů s prostředím
Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Proteiny v metabolismu a při interakci organismů s prostředím
VytisknoutZobrazeno: 27. 11. 2022 06:53