10.1021/cg4012873.s004
Braulio Rodríguez-Molina
Braulio
Rodríguez-Molina
Ma. Eugenia Ochoa
Ma. Eugenia
Ochoa
Margarita Romero
Margarita
Romero
Saeed I. Khan
Saeed I.
Khan
Norberto Farfán
Norberto
Farfán
Rosa Santillan
Rosa
Santillan
Miguel A. Garcia-Garibay
Miguel A.
Garcia-Garibay
Conformational Polymorphism and Isomorphism of Molecular
Rotors with Fluoroaromatic Rotators and Mestranol Stators
American Chemical Society
2013
thermogravimetric analysis
isomorphous structures
Mestranol StatorsWe report
isomorphic crystals
compound 5.
Conformational Polymorphism
Fluoroaromatic Rotators
scanning calorimetry
polymorphic behavior
compounds 3
Molecular Rotors
fluorine atoms
Crystallization experiments
difluoro
isosteric relation
2013-11-06 00:00:00
Dataset
https://acs.figshare.com/articles/dataset/Conformational_Polymorphism_and_Isomorphism_of_Molecular_Rotors_with_Fluoroaromatic_Rotators_and_Mestranol_Stators/2358781
We report the synthesis and characterization
of four molecular
rotors <b>2</b>, <b>3</b>, <b>4</b>, and <b>5</b> containing 2-fluoro-, 2,3-difluoro-, 2,5-difluoro-, and 2,3,5,6-tetrafluoro-substituted
1,4-phenylene rotators, respectively, that are axially linked through
the triple bonds of rigid mestranol (3-methoxy-17α-ethynylestradiol)
stators. Crystallization experiments using solvent mixtures of hexanes–ethyl
acetate and acetonitrile–dichloromethane gave rise to polymorphic,
pseudopolymorphic, and isomorphic crystals. Whereas two solids were
obtained for compound <b>2</b>, four were indentified in the
cases of compounds <b>3</b> and <b>4</b>, and three for
compound <b>5</b>. The 13 solid forms were characterized by
single-crystal and powder X-ray diffraction, infrared spectroscopy,
differential scanning calorimetry, and thermogravimetric analysis.
Two sets of isomorphous structures were obtained for solvated and
solvent-free structures of compounds <b>3</b>–<b>5</b>. While polymorphic behavior of these compounds arises from their
conformational freedom in solution, their isomorphism arises from
the closely isosteric relation that exists between hydrogen and fluorine
atoms.