Hydrogen Bond Binding of Water to Two Cholic Acid Residues

  1. Vázquez-Tato, María Pilar 2
  2. Seijas, Julio A. 2
  3. Meijide, Francisco 1
  4. de Frutos, Santiago 1
  5. Tato, José Vázquez 1
  1. 1 Departamento de Química Física, Facultade de Ciencias, Universidade de Santiago de Compostela, Campus Terra, 27080 Lugo, Spain
  2. 2 Departamento de Química Orgánica, Facultade de Ciencias, Universidade de Santiago de Compostela, Campus Terra, 27080 Lugo, Spain
Actas:
The 26th International Electronic Conference on Synthetic Organic Chemistry

Editorial: MDPI

ISSN: 2673-4583

Año de publicación: 2022

Páginas: 95

Tipo: Aportación congreso

DOI: 10.3390/ECSOC-26-13555 GOOGLE SCHOLAR lock_openAcceso abierto editor

Resumen

Cholic acid is a trihydroxy bile acid with three hydroxy groups at C-3, C-7 and C-12 carbon atoms; two methyl groups at C-10 and C-13 carbon atoms of the steroid nucleus; and a carboxylic group at C24 of the side alkyl chain. The distance between the oxygen atoms linked to C-7 and C-12 (~4.5 Å) perfectly matches with the edge distance between oxygen atoms in ice. This leads to the design of a cholic acid dimer in which one water molecule is encapsulated between two cholic residues, resembling an ice-like structure. The water molecule participates in four hydrogen bonds, the water simultaneously being acceptor from the O12-H hydroxy groups (two bonds with lengths of 2.177 Å and 2.114 Å) and the donor towards the O-7-H groups (two bonds with lengths of 1.866 Å and 1.920 Å). Regarding this communication, we present the application of the “atoms in molecules” (AIM) theory to the tetrahedral structure. The analysis of the calculated electron density, ρ, is performed using its gradient vector, ∇ρ, and the Laplacian, ∇2ρ. The calculation of the complexation energy used correction of the basis set superposition error (BSSE) and the counterpoise method. As expected, four critical (3,−1) points located in the H…O bond paths were identified. All calculated parameters are in concordance with those of similar systems and obey the proposed criteria for hydrogen bonds. The total energy for the interaction is −12.67 kcal/mol and is analysed using proposed energy/electron density equations.

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