Theoretical investigation of ion pair SN2 reactions of alkali isothiocyanates with alkyl halides. Part 1. Reaction of lithium isothiocyanate and methyl fluoride with inversion mechanism

2004 ◽  
Vol 101 (1) ◽  
pp. 104-112 ◽  
Author(s):  
Hua-Jie Zhu ◽  
Yi Ren ◽  
Jie Ren ◽  
San-Yan Chu
Keyword(s):  
Theoretical Investigation ◽  
Ion Pair ◽  
Alkyl Halides ◽  
Methyl Fluoride ◽  
Sn2 Reactions ◽  
Inversion Mechanism

scholarly journals Experimental and theoretical investigation of high- concentration elution bands in ion-pair chromatography

2021 ◽  
Vol 1656 ◽  
pp. 462541
Author(s):  
Marek Leśko ◽  
Jörgen Samuelsson ◽  
Krzysztof Kaczmarski ◽  
Torgny Fornstedt
Keyword(s):  
Theoretical Investigation ◽  
Ion Pair ◽  
High Concentration ◽  
Ion Pair Chromatography

Ion Pair SN2 Reactions. Theoretical Study of Inversion and Retention Mechanisms

1995 ◽  
Vol 117 (11) ◽  
pp. 3253-3259 ◽  
Author(s):  
Sjoerd Harder ◽  
Andrew Streitwieser ◽  
Jeffrey T. Petty ◽  
Paul von Schleyer
Keyword(s):  
Theoretical Study ◽  
Ion Pair ◽  
Retention Mechanisms ◽  
Sn2 Reactions

scholarly journals THE STEREOCHEMISTRY OF HALOGEN DISPLACEMENT BY NITRATE ION RACEMIZATION AND RETENTION OF CONFIGURATION IN THE SYNTHESIS OF DINITRATE ESTERS

1965 ◽  
Vol 43 (6) ◽  
pp. 1656-1660 ◽  
Author(s):  
L. D. Hayward ◽  
M. Jackson ◽  
I. G. Csizmadia
Keyword(s):  
Silver Nitrate ◽  
Steric Effect ◽  
Heterogeneous Reaction ◽  
Ion Pair ◽  
Alkyl Halides ◽  
Preferential Formation ◽  
Carbonium Ion ◽  
Carbonium Ions ◽  
And Inversion ◽  
Derivatives Of

The reaction of silver nitrate in dry acetonitrile with 2,5-dideoxy-2,5-diiodo-1,4;3,6-dianhydro-L-iditol resulted in formation of the dinitrate esters of the 1,4;3,6-dianhydrides of D-mannitol, D-glucitol, and L-iditol. Similarly both endo- and exo-nitrato groups were introduced in displacement of the endo-halogen in the 2-deoxy-2-iodo-5-O-acetyl and 2-deoxy-2-iodo-5-O-p-toluenesulfonyl derivatives of 1,4;3,6-dianhydro-L-iditol. Since both types of nitrato groups were stable to silver nitrate, the racemization occurred during the displacement and was attributed to formation of cyclic carbonium ion intermediates. The steric effect of the adjacent ring in the carbonium ions apparently suppressed the termolecular, ion-pair mechanism previously established for the metathesis of acyclic alkyl halides and caused preferential formation of the exo-nitrato derivatives.The heterogeneous reaction of meso-dibromostilbene with silver nitrate in acetic acid or acetonitrile gave meso-dihydrobenzoin dinitrate with overall retention of configuration. This result could be most readily reconciled with the contrasting sequence of retention and inversion previously reported for meso- and dl-2,3-dibromobutane if participation of neighboring phenyl groups occurred in the second displacement step.

scholarly journals A Theoretical Study of Substituent Effects on Allylic Ion and Ion Pair SN2 Reactions.

ChemInform ◽  
2006 ◽  
Vol 37 (3) ◽  
Author(s):  
A. Streitwieser ◽  
E. G. Jayasree ◽  
S. S.-H. Leung ◽  
G. S.-C. Choy
Keyword(s):  
Theoretical Study ◽  
Substituent Effects ◽  
Ion Pair ◽  
Sn2 Reactions

A determination of W and G(H2) values for methyl fluoride and fluoroform

1970 ◽  
Vol 48 (12) ◽  
pp. 1812-1814 ◽  
Author(s):  
Mario Saca ◽  
R. A. Lee
Keyword(s):  
Gamma Rays ◽  
Ionization Chamber ◽  
Parallel Plate ◽  
Ion Pair ◽  
Methyl Fluoride ◽  
Gray Theory ◽  
Plate Type

Methyl fluoride and fluoroform have been irradiated with gamma rays from a 1200-Ci 60Co source. Ionization currents were measured using a Pyrex parallel-plate-type ionization chamber. W values of 27.2 and 28.0 eV were determined for the two gases, CH3F and CHF3, respectively. The method employed was a comparative one, making use of the Bragg–Gray theory of cavity ionization. G(H2) yields of 4.20 and 1.25 for CH3F and CHF3, respectively, were then calculated from the above W values and the measured ion-pair yields for hydrogen. The formation of hydrogen is probably due to the fact that the C—H bonds in these compounds are weaker than the C—F bonds.

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