Intermediates of Halogen Addition to Phenylethynes and Protonation of Phenylethynyl Halides. Open Halovinyl Cations, Bridged Halonium, or Phenyl-Bridged Ions: A Substituent Effect Study by DFT and GIAO-DFT
Formation of α-phenyl-β-halovinyl cation, β-phenyl-α-halovinyl cation, as well as the halogen-bridged and the spirocyclic phenyl-bridged cations as intermediates of protonation of phenylethynyl halides or by halogen addition to phenylethynes was evaluated by DFT at B3LYP/6-31+G(d) and, for compariso...
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Published in | Journal of organic chemistry Vol. 71; no. 26; pp. 9643 - 9650 |
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Main Authors | , |
Format | Journal Article |
Language | English |
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Washington, DC
American Chemical Society
22.12.2006
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Abstract | Formation of α-phenyl-β-halovinyl cation, β-phenyl-α-halovinyl cation, as well as the halogen-bridged and the spirocyclic phenyl-bridged cations as intermediates of protonation of phenylethynyl halides or by halogen addition to phenylethynes was evaluated by DFT at B3LYP/6-31+G(d) and, for comparison in representative cases, by B3LYP/6-311++G(d,p). Relative stabilities of the resulting minima were gauged as a function of substituents on the phenyl group with p-OH, p-OMe, p-H, p-CF3, p-CN, and p-NO2 and with p-OMeH+, p-NO2H+, and p-N2 +. In the majority of cases, the α-aryl-β-halovinyl cations were identified as the most likely intermediates, irrespective of X and for most R groups. For R = p-N2 + (with X = Br and Cl), R = CNH+ (with X = Cl), and R = MeOH+ (with X = Br), the corresponding β-aryl-α-halovinyl cations become more stable than α-aryl-β-halovinyl cations (but in most cases with a relatively small stability difference). Whereas competitive formation of the spirocyclic aryl bridged cations via this route appears remote, with R = N2 + and R = NO2H+ as substituents (with X = Br), cyclic halonium ions could intervene, since their relative stabilities are within ∼4 kcal/mol of the lowest energy vinyl cations. Geometrical features, GIAO NMR chemical shifts, and NPA-derived charges were used to gain insight into the structural/electronic features in the resulting mono and dications. The study provides a basis for stable ion and solvolytic/kinetic studies on a series of substituted phenylethynyl halides that are being synthesized. |
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AbstractList | Formation of alpha-phenyl-beta-halovinyl cation, beta-phenyl-alpha-halovinyl cation, as well as the halogen-bridged and the spirocyclic phenyl-bridged cations as intermediates of protonation of phenylethynyl halides or by halogen addition to phenylethynes was evaluated by DFT at B3LYP/6-31+G(d) and, for comparison in representative cases, by B3LYP/6-311++G(d,p). Relative stabilities of the resulting minima were gauged as a function of substituents on the phenyl group with p-OH, p-OMe, p-H, p-CF3, p-CN, and p-NO2 and with p-OMeH+, p-NO2H+, and p-N2+. In the majority of cases, the alpha-aryl-beta-halovinyl cations were identified as the most likely intermediates, irrespective of X and for most R groups. For R = p-N2+ (with X = Br and Cl), R = CNH+ (with X = Cl), and R = MeOH+ (with X = Br), the corresponding beta-aryl-alpha-halovinyl cations become more stable than alpha-aryl-beta-halovinyl cations (but in most cases with a relatively small stability difference). Whereas competitive formation of the spirocyclic aryl bridged cations via this route appears remote, with R = N2+ and R = NO2H+ as substituents (with X = Br), cyclic halonium ions could intervene, since their relative stabilities are within approximately 4 kcal/mol of the lowest energy vinyl cations. Geometrical features, GIAO NMR chemical shifts, and NPA-derived charges were used to gain insight into the structural/electronic features in the resulting mono and dications. The study provides a basis for stable ion and solvolytic/kinetic studies on a series of substituted phenylethynyl halides that are being synthesized. Formation of α-phenyl-β-halovinyl cation, β-phenyl-α-halovinyl cation, as well as the halogen-bridged and the spirocyclic phenyl-bridged cations as intermediates of protonation of phenylethynyl halides or by halogen addition to phenylethynes was evaluated by DFT at B3LYP/6-31+G(d) and, for comparison in representative cases, by B3LYP/6-311++G(d,p). Relative stabilities of the resulting minima were gauged as a function of substituents on the phenyl group with p-OH, p-OMe, p-H, p-CF3, p-CN, and p-NO2 and with p-OMeH+, p-NO2H+, and p-N2 +. In the majority of cases, the α-aryl-β-halovinyl cations were identified as the most likely intermediates, irrespective of X and for most R groups. For R = p-N2 + (with X = Br and Cl), R = CNH+ (with X = Cl), and R = MeOH+ (with X = Br), the corresponding β-aryl-α-halovinyl cations become more stable than α-aryl-β-halovinyl cations (but in most cases with a relatively small stability difference). Whereas competitive formation of the spirocyclic aryl bridged cations via this route appears remote, with R = N2 + and R = NO2H+ as substituents (with X = Br), cyclic halonium ions could intervene, since their relative stabilities are within ∼4 kcal/mol of the lowest energy vinyl cations. Geometrical features, GIAO NMR chemical shifts, and NPA-derived charges were used to gain insight into the structural/electronic features in the resulting mono and dications. The study provides a basis for stable ion and solvolytic/kinetic studies on a series of substituted phenylethynyl halides that are being synthesized. |
Author | Okazaki, Takao Laali, Kenneth K |
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Keywords | Substituent effect Stability Acetylenic compound Solvolysis NMR spectrometry Organic halogen compounds Spiran Chemical shift Electronic structure Cyclic compound Halogen compound Vinylic compound Density functional method Protonation Cations Aromatic compound Kinetics Chemical synthesis Organic dication Comparative study |
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Title | Intermediates of Halogen Addition to Phenylethynes and Protonation of Phenylethynyl Halides. Open Halovinyl Cations, Bridged Halonium, or Phenyl-Bridged Ions: A Substituent Effect Study by DFT and GIAO-DFT |
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