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• W2940371112 endingPage "10104" @default.
• W2940371112 startingPage "10095" @default.
• W2940371112 abstract "The first step in the biodegradation of imidazolium-based ionic liquids involves the insertion of the -OH group into the alkyl side chain, and it is believed to be triggered by cytochrome P450. However, at present, there is a lack of fundamental understanding of why the hydroxylation process is observed only for longer alkyl chain analogues. As the initial step of the hydroxylation reaction involves the ionic liquid binding to Fe-porphyrin (FeP) - the catalytic center of cytochrome P450, the orientation of ionic liquids presented to FeP is expected to play a crucial role in eventual hydroxylation of the alkyl side chain. In order to elucidate the chain-length dependent binding preferences exhibited by the homologous series of 1-n-alkyl-3-methylimidazolium (n = 2, 4, 6, 8, and 10) [Cnmim]+ cations, a quantum mechanical treatment of the cations in the presence of free base porphyrin (FBP) and FeP is carried out at the B3LYP-D2 and M06 levels. The binding energy of different complexes with FBP and FeP is investigated by considering three vastly different starting relative orientations of the cations with respect to FBP and FeP: tail down, tail up, and interplanar. Our calculations of binding energies reveal that the cation orientations initiated from the tail down conformations (alkyl chain facing the porphyrin molecules) are progressively destabilized as the alkyl chain length increases. The decomposition of the binding energies into various energetic contributions shows that the interaction energy between the cations and porphyrin molecules varies with the cation geometries presented to porphyrin molecules and is the primary determinant of the magnitude of the binding energies. We further demonstrate that the propensity of the cation-FeP complexes to acquire an electron, the next step in the hydroxylation reaction cycle upon substrate binding, is favored independent of the cations and conformations, suggesting that this step is not the reason for the low biodegradability of short alkyl chain bearing cations. Furthermore, the weaker binding of the ionic liquid to FeP is anticipated to facilitate dioxygen binding to FeP, the step following the electron transfer reaction. Overall, the results of the present calculations indicate that the destabilization of the tail down conformations relative to the other two conformations correlates with the experimental results of the chain length-dependent biodegradation of imidazolium-based ionic liquids." @default.
• W2940371112 created "2019-04-25" @default.
• W2940371112 creator A5004059379 @default.
• W2940371112 creator A5051169860 @default.
• W2940371112 date "2019-01-01" @default.
• W2940371112 modified "2023-09-24" @default.
• W2940371112 title "Insight into conformationally-dependent binding of 1-n-alkyl-3-methylimidazolium cations to porphyrin molecules using quantum mechanical calculations" @default.
• W2940371112 cites W1610261712 @default.
• W2940371112 cites W1805953322 @default.
• W2940371112 cites W1818795018 @default.
• W2940371112 cites W1964289037 @default.
• W2940371112 cites W1970549136 @default.
• W2940371112 cites W1979872108 @default.
• W2940371112 cites W1980222247 @default.
• W2940371112 cites W1980621568 @default.
• W2940371112 cites W1982342550 @default.
• W2940371112 cites W1985818093 @default.
• W2940371112 cites W1990138399 @default.
• W2940371112 cites W1995258983 @default.
• W2940371112 cites W2000087479 @default.
• W2940371112 cites W2017031953 @default.
• W2940371112 cites W2019670461 @default.
• W2940371112 cites W2023082920 @default.
• W2940371112 cites W2025734933 @default.
• W2940371112 cites W2028921476 @default.
• W2940371112 cites W2030961353 @default.
• W2940371112 cites W2032902877 @default.
• W2940371112 cites W2038840267 @default.
• W2940371112 cites W2038935808 @default.
• W2940371112 cites W2043176868 @default.
• W2940371112 cites W2043709433 @default.
• W2940371112 cites W2044591029 @default.
• W2940371112 cites W2046412723 @default.
• W2940371112 cites W2046824682 @default.
• W2940371112 cites W2047259762 @default.
• W2940371112 cites W2048437207 @default.
• W2940371112 cites W2048936184 @default.
• W2940371112 cites W2049233232 @default.
• W2940371112 cites W2052665036 @default.
• W2940371112 cites W2054726270 @default.
• W2940371112 cites W2063818940 @default.
• W2940371112 cites W2064205583 @default.
• W2940371112 cites W2068617439 @default.
• W2940371112 cites W2072486115 @default.
• W2940371112 cites W2073813798 @default.
• W2940371112 cites W2074270054 @default.
• W2940371112 cites W2086461037 @default.
• W2940371112 cites W2086713708 @default.
• W2940371112 cites W2089537078 @default.
• W2940371112 cites W2090699755 @default.
• W2940371112 cites W2092508573 @default.
• W2940371112 cites W2094642658 @default.
• W2940371112 cites W2096881511 @default.
• W2940371112 cites W2100032379 @default.
• W2940371112 cites W2106824077 @default.
• W2940371112 cites W2107310790 @default.
• W2940371112 cites W2111773059 @default.
• W2940371112 cites W2127578078 @default.
• W2940371112 cites W2139213360 @default.
• W2940371112 cites W2140158011 @default.
• W2940371112 cites W2150697053 @default.
• W2940371112 cites W2153513447 @default.
• W2940371112 cites W2163318415 @default.
• W2940371112 cites W2164600977 @default.
• W2940371112 cites W2165492327 @default.
• W2940371112 cites W2288517125 @default.
• W2940371112 cites W2329127475 @default.
• W2940371112 cites W2333687913 @default.
• W2940371112 cites W2465471499 @default.
• W2940371112 cites W2490618334 @default.
• W2940371112 cites W2507582687 @default.
• W2940371112 cites W2557759214 @default.
• W2940371112 cites W2610723124 @default.
• W2940371112 cites W2738965168 @default.
• W2940371112 cites W2784210081 @default.
• W2940371112 cites W2789077910 @default.
• W2940371112 cites W2789555257 @default.
• W2940371112 cites W286029533 @default.
• W2940371112 cites W3205865425 @default.
• W2940371112 cites W4231649355 @default.
• W2940371112 doi "https://doi.org/10.1039/c9cp01538h" @default.
• W2940371112 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/31062770" @default.
• W2940371112 hasPublicationYear "2019" @default.
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