60. Lane JR, Contreras-García J, Piquemal J-P, Miller BJ, Kjaergaard HG (2013) Are bond
critical points really critical for hydrogen bonding? J Chem Theory Comp 9:3263–3266
61. Contreras-García J, Calatayud M, Piquemal J-P, Recio JM (2012) Ionic interactions:
comparative topological approach. Comp Theo Chem 998:193–201
62. Chaudret R, de Courcy B, Contreras-García J, Gloaguen E, Zehnacker-Rentien A, Mons M,
Piquemal J-P (2013) Unraveling non covalent interactions within flexible biomolecules: from
electron density topology to gas phase spectroscopy. Phys Chem Chem Phys 16:9876–9891
63. Spackman MA, Maslen EN (1986) Chemical properties from the promolecule. J Phys Chem
90:2020–2027
64. Martin Pendás A, Luaña V, Pueyo L, Francisco E, Mori-Sánchez P (2002) Hirshfeld surfaces
as approximations to interatomic surfaces. J Chem Phys 117:1017–1023
65. Fiedler S, Broecker J, Keller S (2010) Protein folding in membranes. Cell Mol Life Sci
67:1779–1798
66. Dill KA (1990) Dominant forces in protein folding. Biochemistry 29:7133–7155
67. Deppmeier BJ, Driessen AJ, Hehre W, Johnson JA, Klunzinger PE, Watanabe W (2002)
Spartan ES 1.0.2. Wavefunction Inc., Irvine
68. Lu X-J, Olson WK 3DNA: a software package for the analysis, rebuilding and visualization
of three-dimensional nucleic acid structures. Nucleic Acids Res 31:5108–121
69. http://rutchem.rutgers.edu/olson/Tsukuba/
70. Espinosa E, Molins E, Lecomte C (1988) Hydrogen bond strengths revealed by topological
analyses of experimentally observed electron densities. Chem Phys Lett 285:170–173
71. Wieczorek R, Dannenberg JJ (2004) Comparison of fully optimized α-and 310-helices with
extended β-strands. An oniom density functional theory study. J Am Chem Soc 126:14198–
14205
72. Viswanathan R, Asensio A, Dannenberg JJ (2004) Cooperative hydrogen-bonding in models
of antiparallel β-sheets. J Phys Chem A 108:9205–9212
73. Jurecka P, Hobza P (2003) True stabilization energies for the optimal planar
hydrogen-bonded and stacked structures of guanine. cytosine, adenine. thymine, and their
9-and 1-methyl derivatives: complete basis set calculations at the MP2 and CCSD (T) levels
and comparison with experiment. J Am Chem Soc 125:15608–15613
74. Arunan E, Desiraju GR, Klein RA, Sadlej J, Scheiner S, Alkorta I, Clary DC, Crabtree RH,
Dannenberg JJ, Hobza P, Kjaergaard HG, Legon AC, Mennucci B, Nesbitt DJ (2011)
Definition of the hydrogen bond (IUPAC Recommendations 2011). Pure Appl Chem
83:1637–1641
75. Metrangolo P, Resnati G (2001) Halogen bonding: a paradigm in supramolecular chemistry.
Chem Eur J 7:2511–2519
76. Manna D, Mugesh G (2012) Regioselective deiodination of thyroxine by iodothyronine
deiodinase mimics: an unusual mechanistic pathway involving cooperative chalcogen and
halogen bonding. J Am Chem Soc 134:4269–4279
77. Scheiner S (2011) A new noncovalent force: comparison of P···N interaction with hydrogen
and halogen bonds. J Chem Phys 134:094315–094319
78. Mani D, Arunan E (2013) The X-C···Y (X = O/F, Y = O/S/F/Cl/Br/N/P) ‘carbon bond’ and
hydrophobic interactions. Phys Chem Chem Phys 15:14377–14383
79. Matter H, Nazaré M, Güssregen S, Will DW, Schreuder H, Bauer A, Urmann M, Ritter K,
Wagner M, Wehner V (2009) Evidence for C-Cl/C-Br π interactions as an important
contribution to protein-ligand binding affinity. Angew Chem 121:2955–2960
80. Hardegger LA, Kuhn B, Spinnler B, Anselm L, Ecabert R, Stihle M, Gsell B, Thoma R,
Diez J, Benz J et al (2011) Systematic investigation of halogen bonding in protein-ligand
interactions. Angew Chem Int Ed 50:314–318
81. Peterson KA, Shepler BC, Figgen D, Stoll H (2006) On the spectroscopic and
thermochemical properties of ClO, BrO, IO, and their anions. J Phys Chem A 110:13877–
13883
82. Murray J, Lane P, Politzer P (2007) A predicted new type of directional noncovalent
interaction. Int J Quantum Chem 107:2286–2292
526
C. Narth et al.
critical points really critical for hydrogen bonding? J Chem Theory Comp 9:3263–3266
61. Contreras-García J, Calatayud M, Piquemal J-P, Recio JM (2012) Ionic interactions:
comparative topological approach. Comp Theo Chem 998:193–201
62. Chaudret R, de Courcy B, Contreras-García J, Gloaguen E, Zehnacker-Rentien A, Mons M,
Piquemal J-P (2013) Unraveling non covalent interactions within flexible biomolecules: from
electron density topology to gas phase spectroscopy. Phys Chem Chem Phys 16:9876–9891
63. Spackman MA, Maslen EN (1986) Chemical properties from the promolecule. J Phys Chem
90:2020–2027
64. Martin Pendás A, Luaña V, Pueyo L, Francisco E, Mori-Sánchez P (2002) Hirshfeld surfaces
as approximations to interatomic surfaces. J Chem Phys 117:1017–1023
65. Fiedler S, Broecker J, Keller S (2010) Protein folding in membranes. Cell Mol Life Sci
67:1779–1798
66. Dill KA (1990) Dominant forces in protein folding. Biochemistry 29:7133–7155
67. Deppmeier BJ, Driessen AJ, Hehre W, Johnson JA, Klunzinger PE, Watanabe W (2002)
Spartan ES 1.0.2. Wavefunction Inc., Irvine
68. Lu X-J, Olson WK 3DNA: a software package for the analysis, rebuilding and visualization
of three-dimensional nucleic acid structures. Nucleic Acids Res 31:5108–121
69. http://rutchem.rutgers.edu/olson/Tsukuba/
70. Espinosa E, Molins E, Lecomte C (1988) Hydrogen bond strengths revealed by topological
analyses of experimentally observed electron densities. Chem Phys Lett 285:170–173
71. Wieczorek R, Dannenberg JJ (2004) Comparison of fully optimized α-and 310-helices with
extended β-strands. An oniom density functional theory study. J Am Chem Soc 126:14198–
14205
72. Viswanathan R, Asensio A, Dannenberg JJ (2004) Cooperative hydrogen-bonding in models
of antiparallel β-sheets. J Phys Chem A 108:9205–9212
73. Jurecka P, Hobza P (2003) True stabilization energies for the optimal planar
hydrogen-bonded and stacked structures of guanine. cytosine, adenine. thymine, and their
9-and 1-methyl derivatives: complete basis set calculations at the MP2 and CCSD (T) levels
and comparison with experiment. J Am Chem Soc 125:15608–15613
74. Arunan E, Desiraju GR, Klein RA, Sadlej J, Scheiner S, Alkorta I, Clary DC, Crabtree RH,
Dannenberg JJ, Hobza P, Kjaergaard HG, Legon AC, Mennucci B, Nesbitt DJ (2011)
Definition of the hydrogen bond (IUPAC Recommendations 2011). Pure Appl Chem
83:1637–1641
75. Metrangolo P, Resnati G (2001) Halogen bonding: a paradigm in supramolecular chemistry.
Chem Eur J 7:2511–2519
76. Manna D, Mugesh G (2012) Regioselective deiodination of thyroxine by iodothyronine
deiodinase mimics: an unusual mechanistic pathway involving cooperative chalcogen and
halogen bonding. J Am Chem Soc 134:4269–4279
77. Scheiner S (2011) A new noncovalent force: comparison of P···N interaction with hydrogen
and halogen bonds. J Chem Phys 134:094315–094319
78. Mani D, Arunan E (2013) The X-C···Y (X = O/F, Y = O/S/F/Cl/Br/N/P) ‘carbon bond’ and
hydrophobic interactions. Phys Chem Chem Phys 15:14377–14383
79. Matter H, Nazaré M, Güssregen S, Will DW, Schreuder H, Bauer A, Urmann M, Ritter K,
Wagner M, Wehner V (2009) Evidence for C-Cl/C-Br π interactions as an important
contribution to protein-ligand binding affinity. Angew Chem 121:2955–2960
80. Hardegger LA, Kuhn B, Spinnler B, Anselm L, Ecabert R, Stihle M, Gsell B, Thoma R,
Diez J, Benz J et al (2011) Systematic investigation of halogen bonding in protein-ligand
interactions. Angew Chem Int Ed 50:314–318
81. Peterson KA, Shepler BC, Figgen D, Stoll H (2006) On the spectroscopic and
thermochemical properties of ClO, BrO, IO, and their anions. J Phys Chem A 110:13877–
13883
82. Murray J, Lane P, Politzer P (2007) A predicted new type of directional noncovalent
interaction. Int J Quantum Chem 107:2286–2292
526
C. Narth et al.