86045-83-2Relevant academic research and scientific papers
Directionality of Proton Transfer in Solutions. Three Systems of Known Angularity
Menger, F. M.,Chow, J. F.,Kaiserman, H.,Vasquez, P. C.
, p. 4996 - 5002 (2007/10/02)
Three compounds were synthesized each possessing rigid carbon frameworks that hold an oxygen base near a mobile C-H proton in well-defined angular and distance relationships: 2-iodo-4-hydroxyindan, endo-5-hydroxybicycloheptan-2-one, and endo-2-hydroxy-exo-6-bromomethylheptane.Effective proton transfer was detected with the second and third compounds but not the first.The data suggest that C-to-O proton transfer with severely bent O/H/C angles (106 deg) is permissible if the O-H distance is less than the sum of the van der Waals radii. "Long distance" catalysis at active sites of enzymes appears unlikely.
