Category: OH/pi and NH/pi hydrogen bond

This list is not intended to be comprehensive. A review of interactions with pi-bases appears in Chapter 3 "Other weak and non-conventional hydrogen bonds" in The Weak Hydrogen Bond in Structural Chemistry and Biology, by G. R. Desiraju and T. Steiner, Oxford Univ. Press, 1999.

M. A. Broda et al., J. Peptide Sci. 2005, 11, 235-244: Conformational investigation of ,-dehydropeptides. N-acetyl-(E)-dehydrophenylalanine N'-methylamide: conformational properties from infrared and theoretical studies, part XIV.

T. Korenaga et al., J. Fluorine Chem. 2003, 122, 201-205: Intermolecular oxygen atom/pi interaction in the crystal packing of chiral amino alcohol bearing a pentafluorophenyl group.

K. Goto et al., Chem. Lett. 2003, 1258-1259: Synthesis, structure, and reactions of a novel triarylsilanol with a bowl-type framework: A silanol extremely resistant to self-condensation.

T. Nakanaga et al., Chem. Phys. 2002, 277, 171-178.Weak hydrogen bond interactions in the aniline-alkene (CH2=CH(CH2)nH, n = 0, 1, 2) clusters studied by infrared depletion spectroscopy.

C. M. Reddy et al., CrystEngComm, 2002, 4, 323-325: An engineered NH/pi interaction: crystal structure of 4-tritylbenzamide-p-xylene (2:1).

P. Tarakeshwar and K. S. Kim, J. Molec. Struct. 2002, 615, 227-238: Comparison of the nature of pi and conventional H-bonds: a theoretical investigation.

T. Moriguchi et al., J. Chem. Soc., Perkin Trans. 2 2001, 2084-2088: Preparation and structural properties of dithia[3.3.1]-metacyclophanes.

M. A. Munoz et al., Spectrochim. Acta 2001, 57, 1049-1056: Hydrogen bonding NH/pi interaction between betacarboline and methyl benzene derivatives.

I. Palinko, T. Kortvelyesi, Int. J. Quant. Chem. 2001, 84, 269-275: Structural motifs in a-pyridyl- and a-furylcinnamic acid assemblies - a molecular modeling study.

T. Steiner, G. Koellner, J. Mol. Biol. 2001, 305, 535-557: Hydrogen bonds with pi-acceptors in proteins: Frequencies and role in stabilizing local 3D structures.

T. Steiner et al., New J. Chem. 2001, 25, 174-178: Making very short OH-Ph hydrogen bonds: the example of tetraphenylborate salts.

S. Tsuzuki et al., J. Am. Chem. Soc. 2000, 11450-11458: The origin of the attraction and directionality of the NH/pi interaction: Comparison with OH/pi and CH/pi interactions.

C. Bilton et al., Acta Crystallogr., Sect. B. 2000, 56, 1071-1079: Crystal engineering in the gem-alkynol family; synthon repetitivity and topological similarity in diphenylethynylmethanols: structures that lack OH-O hydrogen bonds.

T. Steiner, S. A. Mason, Acta Crystallogr., Sect. B 2000, 56, 254-260: Short N+H/Ph hydrogen bonds in ammonium tetraphenylborate characterized by neutron diffraction.

B. Twamley et al., J. Organomet. Chem. 2000, 609, 152-160: Sterically encumbered terphenyl substituted primary pnictanes ArEH2 and their metallated derivatives ArE(H)Li (Ar=-C6H3-2,6-Trip2; Trip=2,4,6-triisopropylphenyl; E=N, P, As, Sb).

M. Traetteberg et al., J. Mol. Struct. 2000, 554, 191-202: Intramolecular OH/pi interaction: The molecular structure and conformatons of 3-hexyn-1,6-diol.

O. Dmitrenko et al., THEOCHEM 2000, 530, 85-96: Ab initio study of conformational stability in previtamin D, vitamin D and related model compounds.

P. Tarakeshwar et al., J. Chem. Phys. 1999, 111, 5838-5850: A theoretical investigation of the nature of the pi-H interaction in ethene-H2O, benzene-H2O, and benzene-(H2O)2.

J. F. Gallagher, E. Moriarty, Acta Crystallogr., Sect. C 1999, 55, 1079-1082: Intermolecular (pyrrole)NH-pi(pyrrole) interactions in bis(2-pyrrolyl)methyl-ferrocene, an organometallic porphyrin precursor.

G. Lang. et al., Z. Anorg. Allg. Chem. 1999, 625, 1799-1806: Wasserstoffbruckenbindungen in zweikerkernigen myu-hydroxo-bis[trichloroantimon(V)]-Komplexen mit Phosphat-bzw. Phosphonatgruppen als uberbruckende Liganden.

P. Tarakeshwar et al., J. Chem. Phys. 1998, 108, 7217-7223: Benzene-hydrogen halide interactions: Theoretical studies of binding energies, vibrational frequencies, and equilibrium structures.

S. Kumar et al., J. Molec. Struct. 1998, 448, 51-55: NH/CCH hydrogen bonds as part of cooperative networks: crystal structure of N-(p-methylphenyl)-N-prop-2-ynylurea.

I. Rozas et al., J. Phys. Chem. A 1997, 101, 9457-9463: Unusual hydrogen bonds: H/pi interactions.

K.-S. Kim et al., Chem. Phys. Lett. 1997, 295, 467-502: Quantum mechanical probabilistic structure of the benzene-water complex.

M. Crisma et al., Biopolymers 1997, 42, 1-6: Experimental evidence at atomic resolution for intramolecular NH-pi (phenyl) interactions in a family of amino acid derivatives.

F. H. Allen et al., J. Am. Chem. Soc. 1996, 118, 4081-4084: First neutron diffraction analysis of an O-H/pi hydrogen bond: 2-ethynyladamantan-2-ol.

J. Y. Lee et al., Chem. Phys. Lett. 1995, 232, 67-71: Ab initio study of the complexation of benzene with ammonium cations.

K.-S. Kim et al., J. Am. Chem. Soc. 1994, 116, 7399-7400: On binding forces between aromatic ring and quaternary ammonium compound.

P. K. Bakshi et al., Can. J. Chem. 1994, 72, 1273-1293: Crystal chemistry of tetraradial species. Part 4. Hydrogen bonding to aromatic pi-systems: crystal structures of fifteen tetraphenylborates with organic ammonium cations.

H. S. Rzepa et al., J. Chem. Soc., Perkin Trans. 2 1994, 703-707: A crystallographic, AM1 and PM3 SCF-MO investigation of strong OH/pi-alkene and alkyne hydrogen bonding interactions.

G. Ferguson, J. F. Gallagher, Acta Crystallogr., Sect. C 1994, 50, 70-73: OH-pi(arene) intermolecular hydrogen bonding in the structure of 1,1,2-triphenylethanol.

J. B. O. Mitchell et al., J. Mol. Biol. 1994, 239, 315-331: Amino/aromatic interactions in proteins: Is the evidence stacked against hydrogen bonding?

M. M. Flocco, S. L. Mowbray, J. Mol. Biol. 1994, 235, 709-717: Planar stacking interactions of arginine and aromatic side-chains in proteins.

M. A. Viswamitra et al., J. Am. Chem. Soc. 1993, 115, 4868-4869: Evidence for OH-C and NH-C hydrogen bonding in crystalline alkynes, alkenes, and aromatics.

D. A. Rodham et al., Nature 1993, 362, 735-737: Hydrogen bonding in the benzene-ammonia dimer.

J. Kemmink et al., J. Mol. Biol. 1993, 230, 312-322: Local structure due to an aromatic-amide interaction observed by 1H-Nuclear magnetic resonance spectroscopy in peptides related to the N terminus of bovine pancreatic trypsin inhibitor.

M. F. Perutz, Phil. Trans. R. Soc. A 1993, 345, 105-112: The role of aromatic rings as hydrogen bond acceptors in molecular recognition.

T.-M. Fong et al., Nature 1993, 362, 360-363: Amino-aromatic interaction between histidine 197 of the neurokinin-1 receptor and CP 96345.

L. R. Hanton et al., J. Chem. Soc., Chem. Commun., 1992, 1134-1136: Structural consequences of a molecular assembly that is deficient in hydrogen-bond acceptors.

S. Suzuki et al, Science 1992, 257, 942-945: Benzene forms hydrogen bonds with water.

H.-S. Im et al., J. Am. Chem. Soc. 1991, 113, 4422-4431: Supersonic jet studies of benzyl alcohols: Minimum energy conformations and torsional motion.

J. L. Atwood et al., Nature 1991, 349, 683-684: X-ray diffraction evidence for aromatic pi hydrogen bonding to water.

M. Levitt, M. F. Perutz, J. Mol. Biol. 1988, 201, 751-754: Aromatic rings act as hydrogen bond acceptors.

M. F. Perutz et al., J. Am. Chem. Soc. 1986, 108, 1064-1078: Hemoglobin as a receptor of drugs and peptides: X-ray studies of the stereochemsitry of binding.

S. Ueji et al., Tetrahedron Lett. 1982, 1173-1176: X-ray studies on crystal and molecular structure of 4-nitro-2,6-diphenyl-phenol. Stereochemistry of bifurcated OH-pi hydrogen bonds.

K. Nakatsu et al., Acta Cryst., Sect. B, 1978, 2357-2359: 2,6-Diphenyl-phenol: A structure containing an intramolecular OH-pi hydrogen bond.

A. Aubry et al., Acta Crystallogr., Sect. B 1977, 33, 2572-2578: Structure cristalline du tetraphenylborate de tributylammonium monohydrate: un exemple d'interaction H-pi.

A. D. U. Hardy, D. D. MacNicol, J. Chem. Soc., Perkin Trans., 2, 1976, 1140-1142: Crystal and molecular structure of an OH/pi hydrogen-bonded system: 2,2-bis-(2-hydroxy-5-methyl-3-t-butylphenyl)propane.

H. Iwamura, K. Hanaya, Bull. Chem. Soc. Jpn. 1970, 4, 3901-3908: nyu (greek)O-H Absorptions and conformations of epimeric 1-tetralols and chroman-4-ols.

M. Oki et al., Tetrahedron 1968, 24, 1905-1921: Intramolecular interaction between a hydroxyl group and pi-electrons. XXII. Relationship between conformation and frequency shift by intramolecular OH-pi interaction in olefinic alcohols.

M. Oki, H. Iwamura, J. Am. Chem. Soc. 1967, 89, 576-579: Steric effects on the OH-pi interaction in 2-hydroxybiphenyl.

M. Oki, K. Mutai, Bull. Chem. Soc. Jpn. 1966, 39, 809-813: The intramolecular interaction between the N-H group and pi-electrons. IV. The energetics of the interaction.

Z. Yoshida, E. Osawa, Nippon Kagaku Zasshi, 1966, 87, 509-535: Intermolecular hydrogen bond involving a pi-base as the proton acceptor. (in Japanese)

Z. Yoshida, E. Osawa, J. Am. Chem. Soc. 1965, 87, 1467-1469: Intermolecular hydrogen bond involving a pi-base as the proton acceptor. II. Interaction between phenol and various pi-bases. Preliminary infrared study.

A. T. McPhail, G. A. Sim, Chem. Commun. 1965, 124-126: Hydroxyl-benzene hydrogen bonding: An X-ray study.

H. Iwamura, Kagaku to Kogyo 1964, 17, 617-625: The study of intramolecular interaction between hydroxyl group and pi-electrons [REVIEW].(in Japanese)

H. M. Fales, W. C. Wildman, J. Am. Chem. Soc. 1963, 85, 784-791: Intramolecular hydrogen bonding studies with semi-rigid molecules. I. Derivatives of 5,10b-ethanophenanthridine.

Z. Yoshida, E. Osawa, Kagaku no Ryoiki 1960, 14, 163-173; 248-254: Hydrogen bonding involving pi-electrons as the proton acceptor [REVIEW]. (in Japanese)

G. C. Pimentel, A. L. McClellan, The Hydrogen Bond, W. H. Freeman, San Francisco, 1960, 202: Do aromatics form hydrogen bonds? [BOOK].

M. Oki, Kagaku no Ryoiki 1959, 13, 839-847: Intramolecular interaction between hydroxyl group and pi electrons. [REVIEW]. (in Japanese)

M. Oki, H. Iwamura, Bull. Chem. Soc. Jpn. 1959, 32, 81135-1143: Intramolecular interaction between hydroxyl group and pi electrons. VI. Electronic effect on the interaction in omega-arylalkanols.

M.-L. Josien, G. Sourisseau, Hydrogen Bonding, Pergamon Press, London, D. Hadzi, ed., 1959, 129-137: Contribution a l'etude des molecules aromatiques considerees comme accepteurs de protons [REVIEW].

L. W. Reeves, W. G. Schneider, Can. J. Chem. 1957, 35, 251-261: Nuclear magnetic resonance measurements of complexes of chloroform with aromatic molecules and olefins.

M.-L. Josien, G. Sourisseau, Bull. Soc. Chim. Fr. 1955, 178-183: Le spectre infrarouge de l'acide chlorhydrique en solution. Formation de complexes organiques.

M.-L. Josien et al., Bull. Soc. Chim. Fr. 1955, 1539-1543: Le spectre infrarouge de l'acides bromhydrique eu iodhydrique en solution. Formation de complexes organiques.