XH/pi Interaction (mainly OH/pi and NH/pi)
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.
[NEW] 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.
[NEW] 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.
[NEW] 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, 43, 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.
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.