Rate-limiting proton transfer in .sigma.-complex formation between 1,3,5-trinitrobenzene and N-methylaniline in dimethyl sulfoxide. The differing reactivities of aromatic and aliphatic amines in .sigma.-complex formation and in SNAr processes

Erwin Buncel; Cristobal Innis; Ikenna Onyido

doi:10.1021/jo00369a022

Rate-limiting proton transfer in .sigma.-complex formation between 1,3,5-trinitrobenzene and N-methylaniline in dimethyl sulfoxide. The differing reactivities of aromatic and aliphatic amines in .sigma.-complex formation and in SNAr processes

The Journal of Organic Chemistry ◽

10.1021/jo00369a022 ◽

1986 ◽

Vol 51 (19) ◽

pp. 3680-3686 ◽

Cited By ~ 6

Author(s):

Erwin Buncel ◽

Cristobal Innis ◽

Ikenna Onyido

Keyword(s):

Complex Formation ◽

Proton Transfer ◽

Dimethyl Sulfoxide ◽

Aliphatic Amines ◽

Sigma Complex ◽

Rate Limiting ◽

Aromatic And Aliphatic Amines

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ChemInform Abstract: Rate-Limiting Proton Transfer in δ-Complex Formation between 1,3,5-Trinitrobenzene and N-Methylaniline in Dimethyl Sulfoxide. The Differing Reactivities of Aromatic and Aliphatic Amines in δ-Complex Formation and in SNAr Processes.

ChemInform ◽

10.1002/chin.198713080 ◽

1987 ◽

Vol 18 (13) ◽

Author(s):

E. BUNCEL ◽

C. INNIS ◽

I. ONYIDO

Keyword(s):

Complex Formation ◽

Proton Transfer ◽

Dimethyl Sulfoxide ◽

Aliphatic Amines ◽

Rate Limiting ◽

Aromatic And Aliphatic Amines

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Base catalysis of .sigma.-complex formation between 1,3,5-trinitrobenzene and aniline in dimethyl sulfoxide. Rate limiting proton transfer

Journal of the American Chemical Society ◽

10.1021/ja00460a020 ◽

1977 ◽

Vol 99 (18) ◽

pp. 5958-5964 ◽

Cited By ~ 26

Author(s):

Erwin Buncel ◽

Walter Eggimann

Keyword(s):

Complex Formation ◽

Proton Transfer ◽

Dimethyl Sulfoxide ◽

Base Catalysis ◽

Sigma Complex ◽

Rate Limiting

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ChemInform Abstract: BASE CATALYSIS OF Σ-COMPLEX FORMATION BETWEEN 1,3,5-TRINITROBENZENE AND ANILINE IN DIMETHYL SULFOXIDE. RATE LIMITING PROTON TRANSFER

Chemischer Informationsdienst ◽

10.1002/chin.197750073 ◽

1977 ◽

Vol 8 (50) ◽

pp. no-no

Author(s):

E. BUNCEL ◽

W. EGGIMANN

Keyword(s):

Complex Formation ◽

Proton Transfer ◽

Dimethyl Sulfoxide ◽

Base Catalysis ◽

Rate Limiting

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ChemInform Abstract: INTERMEDIATES IN NUCLEOPHILIC AROMATIC SUBSTITUTION PART 11, SPIRO MEISENHEIMER COMPLEX OF N,N′-DIMETHYL-N-PICRYLETHYLENEDIAMINE, PARTIALLY RATE-LIMITING PROTON TRANSFER OF COMPLEX FORMATION, A TEMPERATURE-JUMP STUDY

Chemischer Informationsdienst ◽

10.1002/chin.197417108 ◽

1974 ◽

Vol 5 (17) ◽

pp. no-no

Author(s):

CLAUDE F. BERNASCONI ◽

CONSTANTIN L. GEHRIGER

Keyword(s):

Complex Formation ◽

Proton Transfer ◽

Temperature Jump ◽

Nucleophilic Aromatic Substitution ◽

Aromatic Substitution ◽

Rate Limiting

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Rate-limiting proton-transfer in the σ-adduct forming reactions of 1,3,5-trinitrobenzene and 4-nitrobenzofuroxan with substituted anilines in dimethyl sulfoxide

Organic & Biomolecular Chemistry ◽

10.1039/b511644a ◽

2005 ◽

Vol 3 (21) ◽

pp. 3971 ◽

Cited By ~ 25

Author(s):

Basim H. M. Asghar ◽

Michael R. Crampton

Keyword(s):

Proton Transfer ◽

Dimethyl Sulfoxide ◽

Substituted Anilines ◽

Rate Limiting

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Intermediates in nucleophilic aromatic substitution. 20. Rate-limiting proton transfer in the formation of Meisenheimer complexes between 1,3,5-trinitrobenzene and amines. The effect of dimethyl sulfoxide on proton-transfer rates. Relative leaving-group abilities of amines and alkoxide ions

The Journal of Organic Chemistry ◽

10.1021/jo01332a020 ◽

1979 ◽

Vol 44 (18) ◽

pp. 3189-3196 ◽

Cited By ~ 28

Author(s):

Claude F. Bernasconi ◽

Morris C. Muller ◽

Peter Schmid

Keyword(s):

Proton Transfer ◽

Dimethyl Sulfoxide ◽

Nucleophilic Aromatic Substitution ◽

Aromatic Substitution ◽

Transfer Rates ◽

Meisenheimer Complexes ◽

Leaving Group ◽

Rate Limiting

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Intermediates in nucleophilic aromatic substitution. XI. Spiro Meisenheimer complex of N, N'-dimethyl-N-picrylethylenediamine. Partially rate-limiting proton transfer of complex formation. Temperature-jump study

Journal of the American Chemical Society ◽

10.1021/ja00811a025 ◽

1974 ◽

Vol 96 (4) ◽

pp. 1092-1099 ◽

Cited By ~ 19

Author(s):

Claude F. Bernasconi ◽

Cvonstantin L. Gehriger

Keyword(s):

Complex Formation ◽

Proton Transfer ◽

Temperature Jump ◽

Nucleophilic Aromatic Substitution ◽

Formation Temperature ◽

Aromatic Substitution ◽

Rate Limiting

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Proton transfer is not rate-limiting in buffer-induced non-enzymic glucation of hemoglobin

Journal of the American Chemical Society ◽

10.1021/ja00232a065 ◽

1988 ◽

Vol 110 (24) ◽

pp. 8265-8266 ◽

Cited By ~ 8

Author(s):

Herminia. Gil ◽

Julio F. Mata-Segreda ◽

Richard L. Schowen

Keyword(s):

Proton Transfer ◽

Rate Limiting

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Intermolecular hydrogen bonds and proton transfer equilibrium in some nitro cresols-aliphatic amines-acetonitrile or methanol systems

Journal of Molecular Liquids ◽

10.1016/s0167-7322(03)00150-8 ◽

2003 ◽

Vol 107 (1-3) ◽

pp. 205-219 ◽

Cited By ~ 7

Author(s):

Moustafa M. Habeeb ◽

Mohamed A. Kharaba

Keyword(s):

Hydrogen Bonds ◽

Proton Transfer ◽

Aliphatic Amines ◽

Intermolecular Hydrogen Bonds

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Proton transfer and complex formation of angiotensin I ions with gaseous molecules at various temperature

Chemical Physics ◽

10.1016/j.chemphys.2013.07.013 ◽

2013 ◽

Vol 423 ◽

pp. 182-191 ◽

Cited By ~ 2

Author(s):

Shinji Nonose ◽

Kazuki Yamashita ◽

Ayako Sudo ◽

Minami Kawashima

Keyword(s):

Complex Formation ◽

Proton Transfer ◽

Angiotensin I

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