FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W788207156> ?p ?o ?g. }

• W788207156 endingPage "29" @default.
• W788207156 startingPage "18" @default.
• W788207156 abstract "Hydrogen phthalate anion has a short strong O–H–O hydrogen bond (H-bond). According to previous experimental studies, the H-bond is asymmetric and two tautomers are interconverted in aqueous solutions. In the present study, the effects of polar solvents on the H-bond in a zwitterionic hydrogen phthalate derivative 1 were investigated by quantum mechanics/molecular mechanics molecular dynamics (MD) simulations. The analyses of the trajectories for the methanol solution showed that the H-bonding proton tends to be located closer to the carboxylate group that forms fewer intermolecular H-bonds, than to the other carboxylate group and that the intramolecular proton transfer in 1 is triggered by the breakage and/or formation of an intermolecular H-bond. The enol form of dibenzoylmethane (2) also has a short H-bond, and the OH bond is reported to be rather long (>1.1 Å) in the crystal. In the present study, the effects of the solvent on the H-bond in 2 were investigated by molecular orbital (MO) calculations, MD simulations and nuclear magnetic resonance (NMR) spectroscopy. Density functional theory (DFT) calculations for 2 in vacuum indicated that the barrier height for the intramolecular proton transfer is almost the same as the zero-point energy of the vibrational ground state, resulting in broad distribution of the proton density along the H-bond, owing to the nuclear quantum effect. The OH distances were determined in CCl4, acetonitrile, and dimethylsulfoxide solutions from the magnetic dipolar interactions between the 17O and 1H nuclei monitoring the nuclear magnetic relaxation times of 1H. The experimental results indicated that the H-bond geometry of 2 is influenced by the interactions with dimethylsulfoxide, suggesting the formation of a bifurcated H-bond, which was supported by the DFT calculations. The MD simulations for the methanol solution of 2 showed that the asymmetry of the OH distance is correlated with the asymmetry in the electrostatic field of the solvent, although the correlation is weaker than that for the methanol solution of 1. The lower sensitivity of 2 to the solvent is attributed to the smaller number of oxygen atoms and the less negative electrostatic potential at the proton-accepting sites. The present study indicates that the specific interactions with protic solvents or strong H-bond-accepting solvents affect the geometry and dynamic behavior of short intramolecular H-bonds." @default.
• W788207156 created "2016-06-24" @default.
• W788207156 creator A5015586043 @default.
• W788207156 creator A5061613158 @default.
• W788207156 date "2015-09-01" @default.
• W788207156 modified "2023-10-18" @default.
• W788207156 title "Effect of solvent on proton location and dynamic behavior in short intramolecular hydrogen bonds studied by molecular dynamics simulations and NMR experiments" @default.
• W788207156 cites W1963781451 @default.
• W788207156 cites W1966325142 @default.
• W788207156 cites W1969642522 @default.
• W788207156 cites W1974209574 @default.
• W788207156 cites W1976161355 @default.
• W788207156 cites W1976197446 @default.
• W788207156 cites W1980971623 @default.
• W788207156 cites W1982359248 @default.
• W788207156 cites W1982982767 @default.
• W788207156 cites W1993568505 @default.
• W788207156 cites W1994676585 @default.
• W788207156 cites W1997093580 @default.
• W788207156 cites W2001775376 @default.
• W788207156 cites W2003949305 @default.
• W788207156 cites W2004814599 @default.
• W788207156 cites W2006020175 @default.
• W788207156 cites W2006804922 @default.
• W788207156 cites W2007640302 @default.
• W788207156 cites W2009218509 @default.
• W788207156 cites W2009325158 @default.
• W788207156 cites W2011912272 @default.
• W788207156 cites W2013155905 @default.
• W788207156 cites W2014184999 @default.
• W788207156 cites W2015335905 @default.
• W788207156 cites W2015421195 @default.
• W788207156 cites W2015726807 @default.
• W788207156 cites W2016802114 @default.
• W788207156 cites W2021670654 @default.
• W788207156 cites W2026590485 @default.
• W788207156 cites W2028741591 @default.
• W788207156 cites W2034499917 @default.
• W788207156 cites W2044462281 @default.
• W788207156 cites W2046679394 @default.
• W788207156 cites W2047224922 @default.
• W788207156 cites W2050300222 @default.
• W788207156 cites W2050532097 @default.
• W788207156 cites W2058363175 @default.
• W788207156 cites W2058848030 @default.
• W788207156 cites W2058957311 @default.
• W788207156 cites W2062293411 @default.
• W788207156 cites W2062849214 @default.
• W788207156 cites W2067174909 @default.
• W788207156 cites W2069801184 @default.
• W788207156 cites W2073297359 @default.
• W788207156 cites W2074001746 @default.
• W788207156 cites W2074092416 @default.
• W788207156 cites W2080648366 @default.
• W788207156 cites W2082545972 @default.
• W788207156 cites W2086634221 @default.
• W788207156 cites W2086786922 @default.
• W788207156 cites W2086946809 @default.
• W788207156 cites W2090361141 @default.
• W788207156 cites W2093381148 @default.
• W788207156 cites W2102103049 @default.
• W788207156 cites W2121371032 @default.
• W788207156 cites W2130409082 @default.
• W788207156 cites W2137419091 @default.
• W788207156 cites W2138800410 @default.
• W788207156 cites W2143981217 @default.
• W788207156 cites W2146462263 @default.
• W788207156 cites W2147993766 @default.
• W788207156 cites W2151263403 @default.
• W788207156 cites W2155450261 @default.
• W788207156 cites W2155986318 @default.
• W788207156 cites W2171283399 @default.
• W788207156 cites W2263298170 @default.
• W788207156 cites W2312414112 @default.
• W788207156 cites W2312760096 @default.
• W788207156 cites W2313285351 @default.
• W788207156 cites W2317805142 @default.
• W788207156 cites W2320217377 @default.
• W788207156 cites W2321499985 @default.
• W788207156 cites W2323998129 @default.
• W788207156 cites W2326354073 @default.
• W788207156 cites W2332712348 @default.
• W788207156 cites W2335441298 @default.
• W788207156 cites W2418503209 @default.
• W788207156 cites W2950219789 @default.
• W788207156 cites W2950403381 @default.
• W788207156 cites W2952067095 @default.
• W788207156 doi "https://doi.org/10.1016/j.chemphys.2015.07.002" @default.
• W788207156 hasPublicationYear "2015" @default.
• W788207156 type Work @default.
• W788207156 sameAs 788207156 @default.
• W788207156 citedByCount "21" @default.
• W788207156 countsByYear W7882071562016 @default.
• W788207156 countsByYear W7882071562017 @default.
• W788207156 countsByYear W7882071562018 @default.
• W788207156 countsByYear W7882071562019 @default.
• W788207156 countsByYear W7882071562021 @default.
• W788207156 countsByYear W7882071562023 @default.

• next