Hydrogen bonding in some t-amino-alcohols related to methadone

1969 ◽  
Vol 47 (9) ◽  
pp. 1587-1592 ◽  
Author(s):  
A. F. Casy ◽  
M. M. A. Hassan
Keyword(s):  
Hydrogen Bonding ◽  
Intramolecular Hydrogen Bonding ◽  
Amino Alcohols ◽  
Frequency Data ◽  
Intramolecular Hydrogen ◽  
Hydrogen Bonded

Hydroxyl stretching frequency data upon 1-dimethylamino-3,3-diphenylhexan-4-ol and related amino-alcohols are reported which give evidence of unusually strong intramolecular hydrogen bonding between the hydroxy and t-amino functions of these compounds. In corresponding salts, concentration independent vOH bands, typical of hydrogen bonded species, also occur and a bonded system comprising anion, OH, and N+H functions is proposed together with probable methadol base and salt conformations.

Photoelectron studies on intramolecularly hydrogen-bonded systems. I. The photoelectron spectra of cis- and trans-2-aminocyclopentanol, and cis- and trans-2-(N,N-dimethylamino)cyclopentanol

1976 ◽  
Vol 54 (4) ◽  
pp. 642-646 ◽  
Author(s):  
R. S. Brown
Keyword(s):  
Hydrogen Bonding ◽  
Ionization Energy ◽  
Lone Pair ◽  
Intramolecular Hydrogen Bonding ◽  
Photoelectron Spectra ◽  
Hydrogen Bonded Systems ◽  
Intramolecular Hydrogen ◽  
Cis And Trans ◽  
Infrared Data ◽  
Hydrogen Bonded

The photoelectron spectra of cis- and trans-2-aminocyclopentanol and cis- and trans-2-(N,N,-dimethylamino)cyclopentanol have been recorded and interpreted. The cis isomers exhibit N lone pair ionizations at higher ionization energy, and O lone pair ionizations at lower ionization energy than their trans isomers.The results are most consistent with the existence and observation of intramolecular hydrogen-bonding in the cis isomers. Infrared data on these systems also show that the cis isomers exist in the intramolecularly hydrogen-bonded state.

1,1-Diphenylbutane-1,3-diol: the First Structurally Characterized Example of an Intramolecularly Hydrogen-Bonded Open-Chain 1,3-diol

1996 ◽  
Vol 49 (11) ◽  
pp. 1251
Author(s):  
CF Carvalho ◽  
DP Arnold ◽  
RC Bott ◽  
G Smith
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Intramolecular Hydrogen Bonding ◽  
Orthorhombic Space Group ◽  
Open Chain ◽  
Space Group ◽  
A Cell ◽  
Intramolecular Hydrogen ◽  
Hydroxy Groups ◽  
Hydrogen Bonded

The crystal structure of the asymmetric 1,3-diol 1,1-diphenylbutane-1,3-diol has been determined and refined to a residual R of 0.039 for 795 observed reflections. Crystals are orthorhombic, space group P212121, with four molecules in a cell of dimensions a 9.625(4), b 16.002(3), c 8.834(3) Ǻ. The compound is unique among the known crystallographically characterized open-chain 1,3-diols in having only intramolecular hydrogen bonding involving the hydroxy groups [O-- -O 2.602(5) Ǻ].

scholarly journals The intramolecular hydrogen bonded–halogen bond: a new strategy for preorganization and enhanced binding

2018 ◽  
Vol 9 (26) ◽  
pp. 5828-5836 ◽  
Author(s):  
Asia Marie S. Riel ◽  
Daniel A. Decato ◽  
Jiyu Sun ◽  
Casey J. Massena ◽  
Morly J. Jessop ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Hydrogen Bonding ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
Intramolecular Hydrogen Bonding ◽  
New Strategy ◽  
Intramolecular Hydrogen ◽  
Hydrogen Bonded

Intramolecular hydrogen bonding directly to halogen bond donors preorganizes molecular structure and strengthens halogen bonding.

DOUBLE-MINIMUM POTENTIAL FOR INTRAMOLECULARLY HYDROGEN-BONDED PROTONS IN ORTHO-SUBSTITUTED ANILINES

1964 ◽  
Vol 42 (2) ◽  
pp. 201-211 ◽  
Author(s):  
P. J. Krueger
Keyword(s):  
Hydrogen Bonding ◽  
Vibrational Level ◽  
Fundamental Mode ◽  
Intramolecular Hydrogen Bonding ◽  
Antisymmetric Mode ◽  
Substituted Anilines ◽  
Minimum Potential ◽  
Intramolecular Hydrogen ◽  
Ortho Substituent ◽  
Hydrogen Bonded

The concentration and temperature-independent splitting of the first overtone NH2 symmetric stretching band in 31 ortho-substituted anilines in which intramolecular hydrogen bonding is possible is interpreted in terms of a double-minimum potential for the hydrogen bonded proton. The intensity ratio of the doublet and the extent of the splitting is related to the basicity of the ortho-substituent, modified by the rigid geometrical restrictions of the intramolecular system. The absence of band splitting in the corresponding fundamental mode suggests that the secondary minimum lies in the vicinity of the v = 2 vibrational level. The antisymmetric mode appears to be less sensitive to perturbations.Deuteration studies, the spectra of some o-substituted N-methyl anilines, and the first over-tone bands of N-methyl aniline in very basic solvents support these views.

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