Absolute rate constants for the reactions of phenylhalocarbenes with alkynes | Zendy

Moss Robert A. | Zendy; Jang Eun G. | Zendy; Ho GuoJie | Zendy

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Absolute rate constants for the reactions of phenylhalocarbenes with alkynes

Author(s) -

Moss Robert A.,

Jang Eun G.,

Ho GuoJie

Publication year - 1990

Publication title -

journal of physical organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.325

H-Index - 66

eISSN - 1099-1395

pISSN - 0894-3230

DOI - 10.1002/poc.610031111

Subject(s) - chemistry , alkyne , alkene , reaction rate constant , entropy of activation , activation energy , medicinal chemistry , computational chemistry , stereochemistry , organic chemistry , kinetics , catalysis , physics , quantum mechanics

Additions of phenylchlorocarbene and phenylfluorocarbene to representative alkynes are rapid (10 6 –10 7 l mol −1 s −1 ). The variation of the rate constants with alkyne structure parallels that observed with analogous alkene substrates. The addition of phenylchlorocarbene to 3‐hexyne is characterized by a very low activation energy (∼ 2 kcal mol −1 ) and a large, negative entropy of activation (∼ −20 e.u.).

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