Model Studies of the Histidine-Tyrosine Cross-Link in Cytochrome c Oxidase Reveal the Flexible Substituent Effect of the Imidazole Moiety
Тип публикации: Journal Article
Дата публикации: 2005-05-27
scimago Q1
wos Q1
БС1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5
ISSN: 15237060, 15237052
PubMed ID:
15957934
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
[reaction: see text] Experimental and theoretical studies were carried out to interrogate the effect of an imidazole substituent in each of the ortho, meta, and para positions on the pK(a), E degrees , and O-H BDE of phenol. The results reveal that imidazole substitution lowers the pK(a) of phenol and increases the E degrees of phenoxide due to its sigma-electron withdrawing ability (sigma(p)(-) = +0.21, sigma(m)(-) = +0.45) but decreases the O-H BDE and E degrees of phenol due to its pi-electron-donating ability (sigma(p)(+) = -0.45).
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Pratt D. A., Pesavento R. P., van der Donk W. A. Model Studies of the Histidine-Tyrosine Cross-Link in Cytochrome c Oxidase Reveal the Flexible Substituent Effect of the Imidazole Moiety // Organic Letters. 2005. Vol. 7. No. 13. pp. 2735-2738.
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Pratt D. A., Pesavento R. P., van der Donk W. A. Model Studies of the Histidine-Tyrosine Cross-Link in Cytochrome c Oxidase Reveal the Flexible Substituent Effect of the Imidazole Moiety // Organic Letters. 2005. Vol. 7. No. 13. pp. 2735-2738.
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TY - JOUR
DO - 10.1021/ol050916g
UR - https://doi.org/10.1021/ol050916g
TI - Model Studies of the Histidine-Tyrosine Cross-Link in Cytochrome c Oxidase Reveal the Flexible Substituent Effect of the Imidazole Moiety
T2 - Organic Letters
AU - Pratt, Derek A.
AU - Pesavento, Russell P
AU - van der Donk, Wilfred A.
PY - 2005
DA - 2005/05/27
PB - American Chemical Society (ACS)
SP - 2735-2738
IS - 13
VL - 7
PMID - 15957934
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2005_Pratt,
author = {Derek A. Pratt and Russell P Pesavento and Wilfred A. van der Donk},
title = {Model Studies of the Histidine-Tyrosine Cross-Link in Cytochrome c Oxidase Reveal the Flexible Substituent Effect of the Imidazole Moiety},
journal = {Organic Letters},
year = {2005},
volume = {7},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/ol050916g},
number = {13},
pages = {2735--2738},
doi = {10.1021/ol050916g}
}
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MLA
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Pratt, Derek A., et al. “Model Studies of the Histidine-Tyrosine Cross-Link in Cytochrome c Oxidase Reveal the Flexible Substituent Effect of the Imidazole Moiety.” Organic Letters, vol. 7, no. 13, May. 2005, pp. 2735-2738. https://doi.org/10.1021/ol050916g.