Hydrogen Bonding Studies. II.<sup>1</sup> The Acidity and Basicity of Silanols Compared to Alcohols<sup>2</sup>

West, Robert; Baney, Ronald H.

doi:10.1021/ja01532a011

Cited by 139 publications

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“…The physicochemical properties, the H-bond acidity and the octanol-water partition coefficient of the tested materials are shown in table 1. The H-bond acidities of the silanols are almost two times higher than their analogous alcohols due to the electron back donation through π-bonding from a p orbital of oxygen to a vacant d orbital of silicon [23]. This greater acidity occurs even though the silicon atom is more electropositive than a carbon atom, which would lead one to predict that silanols should be less acidic than their analogous carbinols.…”

Section: Characterization Of the Partition Coefficient The H-bond Acmentioning

confidence: 99%

“…Relative H-bond acidities of a series of silanols, analogous alcohols, and phenols were determined by measuring ∆ν, defined as the shift in frequency of the O-H stretching band between free OH and OH hydrogen-bonded to diethyl ether oxygen [23]. The shift, ∆ν, is proportional to the strength of the hydrogen bond.…”

Section: Measurement Of Hydrogen-bond Acidity (H-bond Acidity)mentioning

confidence: 99%

“…One-to-one mixtures of the base and the silanols or alcohols were prepared for the infrared spectroscopy study. The possibility of the self-association bands was not a concern at the low concentration of silanols and alcohols [23].…”

Section: Measurement Of Hydrogen-bond Acidity (H-bond Acidity)mentioning

confidence: 99%

“…A broad OH band was detected at lower frequency range, 3500-3200 cm -1 , due to OH hydrogen bonded to the ether oxygen, whereas a sharp free-OH band was observed at higher frequency, 3800-3550 cm -1 . The difference in frequency between two bands, ∆ν, measured the relative H-bonding acidity of the silanols and alcohols [23].…”

Section: Measurement Of Hydrogen-bond Acidity (H-bond Acidity)mentioning

confidence: 99%

“…The hydrogen-bonding forces are directly related to the H-bond acidity [23]. It is reasonable to suggest that the higher H-bond acidity of the silanols compared to the analogous alcohols has contributed to a better balance through strong hydrogen bonding.…”

Section: Structure and Antimicrobial Activity Relationshipmentioning

confidence: 99%

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Structure--Antimicrobial Activity Relationship Comparing a New Class of Antimicrobials, Silanols, to Alcohols and Phenols

Kim¹,

Farrah²,

Baney³

2006

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Standard Form 298 (Rev. 8/98) REPORT DOCUMENTATION PAGEPrescribed by ANSI Std. Z39.18 Form Approved OMB No. 0704-0188The public reporting burden for this collection of information is estimated to average 1 hour per response, including the time for reviewing instructions, searching existing data sources, gathering and maintaining the data needed, and completing and reviewing the collection of information. Send comments regarding this burden estimate or any other aspect of this collection of information, including suggestions for reducing the burden, Alkyldimethylsilanols, R(CH 3 ) 2 SiOH, were recently reported to exhibit unexpectedly strong antimicrobial effects. The antimicrobial activities of alkyldimethylsilanols were significantly higher than their analogous alcohols. A study of structural dependence of their antimicrobial activity was conducted with four bacteria, Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, and Enterococcus faecalis. Silanols, alcohols with structures analogous to the silanols, R(CH 3 ) 2 COH, and substituted phenols were evaluated as a single class of materials. The minimum lethal concentrations (MLC) defined as the concentration required for a 7-log reduction in viable bacteria after a 1-hour exposure period were used to measure the antimicrobial activity. Octanol/water partition coefficients (log P) and H-bond acidities (Continued on p. ii) (∆ν) measured as the shift in frequency of O-H stretching bands between free OH and hydrogen bonded OH to diethyl ether oxygen by infrared spectroscopy were utilized as a dispersive and polar structural parameter. The correlation established by multiple regression analysis between antimicrobial activities and structural properties of silanols and carbinols against the four bacteria was log (1/MLC) = 0.670 log P + 0.0035 ∆ν -1.836, n = 282, r = 0.96, s = 0.22. This equation and a significantly high correlation coefficient r supported the hypothesis that the lipophilic properties and the H-bond acidities are primary factors for antimicrobial action of silanols and carbinols. PERFORMING ORGANIZATION NAME(S) AND ADDRESS(ES) 8. PERFORMING ORGANIZATION REPORT NUMBER SPONSORING/MONITORING AGENCY NAME(S) AND ADDRESS(ES) 10. SPONSOR/MONITOR'S ACRONYM(S) SPONSOR/MONITOR'S REPORT NUMBER(S)ii

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Section: Characterization Of the Partition Coefficient The H-bond Acmentioning

confidence: 99%

Section: Measurement Of Hydrogen-bond Acidity (H-bond Acidity)mentioning

confidence: 99%

Section: Measurement Of Hydrogen-bond Acidity (H-bond Acidity)mentioning

confidence: 99%

Section: Measurement Of Hydrogen-bond Acidity (H-bond Acidity)mentioning

confidence: 99%

Section: Structure and Antimicrobial Activity Relationshipmentioning

confidence: 99%

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