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Self-recognition and hydrogen bonding by polycyclic bridgehead monoalcohols
Amelia García Fraile1, David G Morris, Antonio García Martínez
1Departamento de Química Orgánica y Biología, Facultad de Ciencias, Universidad Nacional de Educación a Distancia, Senda del Rey 9, 28040-Madrid, Spain.
Organic & Biomolecular Chemistry
|August 22, 2003
Summary
This study reveals how hydrogen bonding in polycyclic monoalcohols influences crystal structures. Specific motifs, like helices and rings, are observed, offering insights into solid-state properties.
Area of Science:
- Solid-state chemistry
- Crystallography
- Organic chemistry
Background:
- Hydrogen bonding is crucial in determining the properties of molecular solids.
- Polycyclic bridgehead monoalcohols present unique structural challenges and opportunities for hydrogen bonding.
- Understanding these relationships is key to predicting and controlling material properties.
Purpose of the Study:
- To determine the crystal structures of three polycyclic bridgehead monoalcohols.
- To investigate the hydrogen bonding motifs present in these structures.
- To compare these motifs with those found in other tertiary monoalcohols.
Main Methods:
- Single-crystal X-ray diffraction was used to determine the crystal structures.
- Analysis of hydrogen bonding networks, including helices and rings, was performed.
- A survey of the Cambridge Structural Database was conducted for comparison.
Main Results:
- One C10H16O isomer formed an infinite helix via hydrogen bonds.
- A second C10H16O isomer formed rings of four molecules through cooperative hydrogen bonds.
- A related keto-alcohol formed infinite chains via C-OH...O=C hydrogen bonding.
Conclusions:
- The observed hydrogen bonding motifs are typical for tertiary monoalcohols.
- Tertiary monoalcohols show a preference for trigonal and tetragonal space groups.
- Asymmetric units containing multiple molecules are characteristic of tertiary monoalcohol crystallography.