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Volumn 62, Issue 12, 1997, Pages 4036-4046

Single-Step and Multistep Mechanisms of Aromatic Nucleophilic Substitution of Halobenzenes and Halonitrobenzenes with Halide Anions: Ab Initio Computational Study

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Indexed keywords


EID: 0000799038     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962096e     Document Type: Article
Times cited : (71)

References (111)
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    • For a discussion of the current status of the electronegativity concept in chemistry and for leading references, see: (a) Allen, L. C. Int. J. Quant. Chem. 1994, 49, 253. (b) Allen, L. C. J. Am. Chem. Soc. 1989, 111, 9003.
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    • note
    • 5X fragment in 2, which are caused by the complexation, are largest for X = F. While the C-H bond for the hydrogen coordinated with the incoming halide anion is only 0.006, 0.005, and 0.003 Å longer in 2b-d, respectively, than that in corresponding halobenzenes 1b-d, the C-H bond in 2a (1.118 Å) is elongated by 0.031 Å as compared with the C-H bond in fluorobenzene calculated at the MP2/6-31+G(d) level (Table 2 and Table 2S). The halide complexation leads to a slight elongation of the C-X bond length in 2a-d when compared with that in the halobenzenes.
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    • note
    • 40c
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    • NAr reactions.
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    • note
    • -1.
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    • We do not consider the nonidentity reactions with a different nucleophile and leaving group
    • We do not consider the nonidentity reactions with a different nucleophile and leaving group.
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    • note
    • 51
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