What factors determine whether a proton-bound homodimer has a symmetric or an asymmetric hydrogen bond?

References

• Jeffrey , GA . 1997 . An Introduction to Hydrogen Bonding , New York : Oxford University Press . For recent reviews, see:
   Google Scholar
• Scheiner , S . 1997 . Hydrogen Bonding: A Theoretical Perspective , New York : Oxford University Press .
   Google Scholar
• Scheiner , S . 1997 . Molecular Interactions: From van der Waals to Strongly Bound Complexes , Chichester : John Wiley and Sons .
   Google Scholar
• Grabowski , SJ . 2006 . Hydrogen Bonding–New Insights , Dordrecht : Springer .
   Google Scholar
• Buckingham , AD , Del Bene , JE and McDowell , SAC . 2008 . Chem. Phys. Lett , 463 : 1
   Web of Science ®Google Scholar
• Remer , LC and Jensen , JH . 2000 . J. Phys. Chem. A , 104 : 9266
   Web of Science ®Google Scholar
• Frey , PA . 2001 . Magn. Reson. Chem. , 39 : S190
   Google Scholar
• Grabowski , SJ and Sokalski , WA . 2005 . J. Phys. Org. Chem. , 18 : 779
   Web of Science ®Google Scholar
• Hibbert , F and Emsley , J . 1990 . Adv. Phys. Org. Chem. , 26 : 255
   Google Scholar
• Schiøtt , B , Iversen , BB , Madsen , GKH and Bruice , TC . 1998 . Proc. Natl. Acad. Sci. USA , 95 : 12799
   PubMed Web of Science ®Google Scholar
• Overgaard , J , Schiøtt , B Larsen , FK . 1999 . Angew. Chem., Int. Ed. , 38 : 1239
   Web of Science ®Google Scholar
• Gilli , P , Bertolasi , V , Ferretti , V and Gilli , G . 2000 . J. Am. Chem. Soc. , 122 : 10405
   Web of Science ®Google Scholar
• Gilli , G and Gilli , P . 2000 . J. Mol. Struct. , 552 : 1
   Web of Science ®Google Scholar
• Pauling , LC . 1960 . The Nature of the Chemical Bond , New York : Cornell University Press .
   Google Scholar
• Desiraju , G and Steiner , T . 1999 . The Weak Hydrogen Bond in Structural Chemistry and Biology , New York : Oxford University Press .
   Google Scholar
• Marechal , Y . 2007 . The Hydrogen Bond and the Water Molecule: The Physics and Chemistry of Water, Aqueous and Biomedia , Amsterdam : Elsevier .
   Google Scholar
• Fersht , AR . 1985 . Enzyme Structure and Mechanism , 2nd , New York : W.H. Freeman & Company .
   Google Scholar
• Franks , F . 1988 . Characterization of Proteins , Clifton : Humana Press .
   Google Scholar
• Kirby , AJ . 1997 . Accts Chem. Res. , 30 : 290
   Web of Science ®Google Scholar
• Zeegers-Huyskens , T and Mol. , J . 1988 . Struct. , 177 : 125
   Google Scholar
• Humbel , S , Hoffmann , N , Cote , I and Bouquant , J . 2000 . Chem. Eur. J. , 6 : 1592
   PubMed Web of Science ®Google Scholar
• Humbel , S . 2002 . J. Phys. Chem. A , 106 : 5517
   Google Scholar
• Bian , L . 2003 . J. Phys. Chem. A , 107 : 11517
   Web of Science ®Google Scholar
• Del Bene , JE , Elguero , J and Alkorta , I . 2007 . J. Phys. Chem. A , 111 : 3416 Notable exceptions occur, however, in proton-bound dimers containing third-row elements:
   PubMed Web of Science ®Google Scholar
• Pudzianowski , AT . 1995 . J. Chem. Phys. , 102 : 8029 For discussions of proton-bound homodimers, see, for example:
   Web of Science ®Google Scholar
• Perrin , CL and Nielson , JB . 1997 . Annu. Rev. Phys. Chem. , 48 : 511
   PubMed Web of Science ®Google Scholar
• Mayer , PM . 1999 . J. Chem. Phys. , 110 : 7779
   Web of Science ®Google Scholar
• Meot-Ner , M . 2005 . Chem. Rev. , 105 : 213
   PubMed Web of Science ®Google Scholar
• Grabowski , SJ . 2006 . Annu. Rep. Prog. Chem., Sect. C: Phys. Chem. , 102 : 131
   Google Scholar
• Bürgi , HB and Dunitz , JD . 1983 . Acc. Chem. Res. , 16 : 153
   Web of Science ®Google Scholar
• Bürgi , HB and Dunitz , JD . 1994 . Structure Correlation , Vol. 1 , 197 Weinheim : VCH .
   Google Scholar
• Chan , B , Del Bene , JE and Radom , L . 2007 . J. Am. Chem. Soc. , 129 : 12197
   PubMed Web of Science ®Google Scholar
• Hehre , WJ , Radom , L , Schleyer , PV and Pople , JA . 1986 . Ab Initio Molecular Orbital Theory , New York : Wiley .
   Google Scholar
• Jensen , F . 1998 . Introduction to Computational Chemistry , 2nd , Chichester : John Wiley & Sons .
   Google Scholar
• Frisch , MJ , Trucks , GW , Schlegel , HB , Scuseria , GE , Robb , MA , Cheeseman , JR , Zakrzewski , VG , Montgomery , JA , Stratmann , RE , Burant , JC , Dapprich , S , Millam , JM , Daniels , AD , Kudin , KN , Strain , MC , Farkas , O , Tomasi , J , Barone , V , Cossi , M , Cammi , R , Mennucci , B , Pomelli , C , Adamo , C , Clifford , S , Ochterski , J , Petersson , GA , Ayala , PY , Cui , Q , Morokuma , K , Malick , DK , Rabuck , AD , Raghavachari , K , Foresman , JB , Cioslowski , J , Ortiz , JV , Baboul , AG , Stefanov , BB , Liu , G , Liashenko , A , Piskorz , P , Komaromi , I , Gomperts , R , Martin , RL , Fox , DJ , Keith , T , Al-Laham , MA , Peng , CY , Nanayakkara , A , Gonzalez , C , Challacombe , M , Gill , PMW , Johnson , BG , Chen , W , Wong , MW , Andres , JL , Head-Gordon , M , Replogle , ES and Pople , JA . 2004 . Gaussian 03, Revision D.02 , Wallingford CT : Gaussian, Inc. .
   Google Scholar
• Curtiss , LA , Raghavachari , K , Redfern , PC and Pople , JA . 1998 . J. Chem. Phys. , 109 : 7764 The G3MP2Large basis set is similar to the 6-311+G(3df,2p) basis set but employs 3d21f on second-row and 2d1f polarization functions on first-row elements. See:
   Web of Science ®Google Scholar
• Curtiss , LA , Redfern , PC , Raghavachari , K , Rassolov , V and Pople , JA . 1999 . J. Chem. Phys. , 110 : 4703
   Web of Science ®Google Scholar
• Henry , DJ , Sullivan , MB and Radom , L . 2003 . J. Chem. Phys. , 118 : 4849
   Web of Science ®Google Scholar
• Reed , AE , Curtiss , LA and Weinhold , F . 1988 . Chem. Rev , 88 : 899
   Web of Science ®Google Scholar