PMID- 15962275
OWN - NLM
STAT- MEDLINE
DCOM- 20050825
LR  - 20131121
IS  - 0192-8651 (Print)
IS  - 0192-8651 (Linking)
VI  - 26
IP  - 12
DP  - 2005 Sep
TI  - Conformations, energies, and intramolecular hydrogen bonds in dicarboxylic acids: 
      implications for the design of synthetic dicarboxylic acid receptors.
PG  - 1233-41
AB  - The various conformers of the dicarboxylic acids HO2C--(CH2)n--CO2H, n = 1-4, 
      were obtained using density functional methods (DFT), both in the gas phase and 
      in the aqueous phase using a polarized continuum model (PCM). Several new 
      conformers were identified, particularly for the two larger molecules glutaric (n 
      = 3) and adipic acid (n =4). The PCM results show that the stability of most 
      conformers were affected, many becoming unstable in the aqueous phase; and the 
      energy ordering of conformers is also different. The results suggest that 
      conformational preferences could be important in determining the design and 
      stability of appropriate synthetic receptors for glutaric and adipic acid. 
      Geometry changes between gas and aqueous phases were most marked in those 
      conformers containing an intramolecular hydrogen bond. Additional calculations 
      have probed the strength of intramolecular hydrogen bonds in these dicarboxylic 
      acids. In the cases of glutaric and adipic acid, the strength of the 
      intramolecular hydrogen bond were estimated to be around 28-29 kJ/mol, without 
      any vibrational energy correction. The intramolecular hydrogen bond energies in 
      malonic and succinic acid were also estimated from the calculated H-bond 
      distances using an empirical relationship. Intramolecular H-bond redshifts of 
      170-250 cm(-1) have been estimated from the results of the harmonic frequency 
      analyses.
CI  - (c) 2005 Wiley Periodicals, Inc.
FAU - Nguyen, Thanh Ha
AU  - Nguyen TH
AD  - Faculty of Pharmacy, University of Sydney, NSW 2006, Australia.
FAU - Hibbs, David E
AU  - Hibbs DE
FAU - Howard, Sian T
AU  - Howard ST
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PL  - United States
TA  - J Comput Chem
JT  - Journal of computational chemistry
JID - 9878362
RN  - 0 (Adipates)
RN  - 0 (Dicarboxylic Acids)
RN  - 0 (Glutarates)
RN  - 0 (Malonates)
RN  - 76A0JE0FKJ (adipic acid)
RN  - 9KX7ZMG0MK (malonic acid)
RN  - AB6MNQ6J6L (Succinic Acid)
RN  - H849F7N00B (glutaric acid)
SB  - IM
MH  - Adipates/chemistry
MH  - Dicarboxylic Acids/*chemistry
MH  - Glutarates/chemistry
MH  - Hydrogen Bonding
MH  - Isomerism
MH  - Malonates/chemistry
MH  - *Models, Molecular
MH  - Molecular Conformation
MH  - Molecular Structure
MH  - Succinic Acid/chemistry
MH  - Thermodynamics
EDAT- 2005/06/18 09:00
MHDA- 2005/08/27 09:00
CRDT- 2005/06/18 09:00
PHST- 2005/06/18 09:00 [pubmed]
PHST- 2005/08/27 09:00 [medline]
PHST- 2005/06/18 09:00 [entrez]
AID - 10.1002/jcc.20259 [doi]
PST - ppublish
SO  - J Comput Chem. 2005 Sep;26(12):1233-41. doi: 10.1002/jcc.20259.