Detail of "163682-35-7"

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Theoretical Study of Intramolecular SN2 Reactions of 3-Halogen or 3-Hydroxypropanamides To Obtain b-Lactams

Theoretical Study of Intramolecular SN2 Reactions of 3-Halogen or 3-Hydroxypropanamides To Obtain b-Lactams. Campomanes, Pablo; Menendez, M. Isabel; Sordo, Tomas L. ( Departamento de Quimica Fisica y Analitica, Facultad de Quimica, Universidad de Oviedo, Oviedo, Principado de Asturias 33006, Spain). Journal of Physical Chemistry A, 108(50), 11109-11115 (English) 2004 American Chemical Society. CODEN: JPCAFH. ISSN: 1089-5639. DOCUMENT TYPE: Journal CA Section: 22 (Physical Organic Chemistry) A theor. study of the intramol. cyclization of a series of propanamides to yield b-lactams was performed at the B3LYP/6-31+G(d,p) and MP2/6-31+G(d,p)//B3LYP/6-31+G(d,p) levels. The effect of the Cl- and OH- leaving groups and of several substituents on N1 and on C4 was investigated. As expected, OH- is a much worse leaving group than Cl-, rendering an energy barrier about 2 times larger. 163682-35-7 and 14280-30-9 which are cas registry numbers of chemicals are mentioned. An SO3- substituent on N1 diminishes the energy barrier by destabilizing the intermediate prior to the rate-detg. TS, whereas OH and OCH3 substituents do not produce an appreciable effect. According to the MP2 method, one and two Me substituents on C4 increase the energy barrier of the process. The simultaneous presence of a sulfonate group on N1 and a Me group on C4 render the corresponding combined effect, while combination of an OH on N1 and two Me groups on C4 is not simply additive. .