Matches in SemOpenAlex for { <https://semopenalex.org/work/W2081529187> ?p ?o ?g. }
- W2081529187 endingPage "2943" @default.
- W2081529187 startingPage "2937" @default.
- W2081529187 abstract "Among the weak intermolecular interactions found in proteins, the amide N--H...pi interaction has been widely observed but remains poorly characterized as an individual interaction. We have investigated the isolated supersonic-jet-cooled dimer of the cis-amide and nucleobase analogue 2-pyridone (2PY) with benzene and benzene-d6. Both MP2 and SCS-MP2 geometry optimizations yield a T-shaped structure with a N--H...pi hydrogen bond to the benzene ring and the C=O group above, but far from the C--H bonds of benzene. The CCSD(T) calculated binding energy at the optimum geometry is De = 25.2 kJ/mol (dissociation energy D0 = 21.6 kJ/mol), corresponding to the H-bond strength of the water dimer or of N--H...O hydrogen bonds. The T-shaped geometry is supported by the infrared-ultraviolet depletion spectra of 2PY x benzene: The N--H stretch vibrational frequency is lowered by 56 cm(-1), and the C=O stretch vibration is lowered by 10 cm(-1), relative to those of bare 2PY, indicating a strong N--H...pi interaction and a weak interaction of the C=O group. The benzene C--H infrared stretches exhibit very small shifts (approximately 2 cm(-1)) relative to benzene, signaling the absence of interactions with the benzene C--H groups. The infrared spectral shifts are consistent with a strong nonconventional pi hydrogen bond and a T-shaped structure for 2PY x benzene. Symmetry-adapted perturbation theory calculations show that the N--H...pi interaction is by far the dominant stabilization factor." @default.
- W2081529187 created "2016-06-24" @default.
- W2081529187 creator A5014682778 @default.
- W2081529187 creator A5022251442 @default.
- W2081529187 creator A5042905549 @default.
- W2081529187 creator A5047689767 @default.
- W2081529187 creator A5049718224 @default.
- W2081529187 creator A5066767077 @default.
- W2081529187 date "2009-02-10" @default.
- W2081529187 modified "2023-10-16" @default.
- W2081529187 title "Strong N−H···π Hydrogen Bonding in Amide−Benzene Interactions" @default.
- W2081529187 cites W1963616108 @default.
- W2081529187 cites W1969510290 @default.
- W2081529187 cites W1970466183 @default.
- W2081529187 cites W1974431580 @default.
- W2081529187 cites W1986856991 @default.
- W2081529187 cites W1990588332 @default.
- W2081529187 cites W1992723417 @default.
- W2081529187 cites W1999947210 @default.
- W2081529187 cites W2000125153 @default.
- W2081529187 cites W2000242754 @default.
- W2081529187 cites W2000321895 @default.
- W2081529187 cites W2001786168 @default.
- W2081529187 cites W2012609329 @default.
- W2081529187 cites W2018801628 @default.
- W2081529187 cites W2020130870 @default.
- W2081529187 cites W2020777248 @default.
- W2081529187 cites W2024885511 @default.
- W2081529187 cites W2028022118 @default.
- W2081529187 cites W2030837735 @default.
- W2081529187 cites W2032204983 @default.
- W2081529187 cites W2036248673 @default.
- W2081529187 cites W2036668937 @default.
- W2081529187 cites W2042646436 @default.
- W2081529187 cites W2043833690 @default.
- W2081529187 cites W2044098935 @default.
- W2081529187 cites W2044672033 @default.
- W2081529187 cites W2044998649 @default.
- W2081529187 cites W2048631643 @default.
- W2081529187 cites W2050833307 @default.
- W2081529187 cites W2051762921 @default.
- W2081529187 cites W2055757758 @default.
- W2081529187 cites W2056705026 @default.
- W2081529187 cites W2060456589 @default.
- W2081529187 cites W2065486400 @default.
- W2081529187 cites W2070203126 @default.
- W2081529187 cites W2071268775 @default.
- W2081529187 cites W2072997098 @default.
- W2081529187 cites W2074821401 @default.
- W2081529187 cites W2076353005 @default.
- W2081529187 cites W2077416151 @default.
- W2081529187 cites W2080796053 @default.
- W2081529187 cites W2090496422 @default.
- W2081529187 cites W2091309429 @default.
- W2081529187 cites W2091700214 @default.
- W2081529187 cites W2093962746 @default.
- W2081529187 cites W2116112181 @default.
- W2081529187 cites W2139842482 @default.
- W2081529187 cites W2141352913 @default.
- W2081529187 cites W2146237323 @default.
- W2081529187 cites W2161228776 @default.
- W2081529187 doi "https://doi.org/10.1021/jp8110474" @default.
- W2081529187 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/19243205" @default.
- W2081529187 hasPublicationYear "2009" @default.
- W2081529187 type Work @default.
- W2081529187 sameAs 2081529187 @default.
- W2081529187 citedByCount "102" @default.
- W2081529187 countsByYear W20815291872012 @default.
- W2081529187 countsByYear W20815291872013 @default.
- W2081529187 countsByYear W20815291872014 @default.
- W2081529187 countsByYear W20815291872015 @default.
- W2081529187 countsByYear W20815291872016 @default.
- W2081529187 countsByYear W20815291872017 @default.
- W2081529187 countsByYear W20815291872018 @default.
- W2081529187 countsByYear W20815291872019 @default.
- W2081529187 countsByYear W20815291872020 @default.
- W2081529187 countsByYear W20815291872021 @default.
- W2081529187 countsByYear W20815291872022 @default.
- W2081529187 countsByYear W20815291872023 @default.
- W2081529187 crossrefType "journal-article" @default.
- W2081529187 hasAuthorship W2081529187A5014682778 @default.
- W2081529187 hasAuthorship W2081529187A5022251442 @default.
- W2081529187 hasAuthorship W2081529187A5042905549 @default.
- W2081529187 hasAuthorship W2081529187A5047689767 @default.
- W2081529187 hasAuthorship W2081529187A5049718224 @default.
- W2081529187 hasAuthorship W2081529187A5066767077 @default.
- W2081529187 hasBestOaLocation W20815291871 @default.
- W2081529187 hasConcept C102931765 @default.
- W2081529187 hasConcept C112887158 @default.
- W2081529187 hasConcept C147789679 @default.
- W2081529187 hasConcept C166950319 @default.
- W2081529187 hasConcept C178790620 @default.
- W2081529187 hasConcept C185592680 @default.
- W2081529187 hasConcept C2777691172 @default.
- W2081529187 hasConcept C2778439535 @default.
- W2081529187 hasConcept C2779546866 @default.
- W2081529187 hasConcept C32909587 @default.
- W2081529187 hasConcept C62396407 @default.