title: Comparative study of the H-bond and FTIR spectra between 2,2-hydroxymethyl propionic acid and 2,2-hydroxymethyl butanoic acid.
abstract: In the present paper, the FTIR band and H-bond differences between the two dihydroxy-based carboxyls, 2,2-hydroxymethyl butanoic acid (hereinafter abbreviated to DMBA) and 2,2-hydroxymethyl propionic acid (hereinafter abbreviated to DMPA), were analyzed based on the crystal structure as well as the relation between H-bond and FTIR band of DMPA. In addition, the energy and length of the H-bonds formed between COOH, between OH, between COOH and OH were also calculated via molecular modeling. The results showed that three H-bond types existing in DMPA while only two in DMBA. The COOH pattern and H-bond type in DMBA and DMPA can be preliminarily judged according to the band position and relative strength of the nuOH and nuCOOH in FTIR spectrum. The H atom in COOH is a stronger H-bond donor than that in primary OH, while the O atom in primary OH is a stronger H-bond acceptor than that in COOH. The H-bond formed by two COOH is, therefore, weaker than that formed by COOH (as donor) and OH (as acceptor), which makes nuC=O shift to lower frequency in DMPA than in DMBA.
authors.affiliation: Henan Key Lab of Fine Chemicals, Zhengzhou 450002, PR China.
authors.forename: Jing
authors.initials: J
authors.lastname: Zhu
authors.forename: Zhiyong
authors.initials: Z
authors.lastname: Ren
authors.forename: Guobao
authors.initials: G
authors.lastname: Zhang
authors.forename: Xiaozhan
authors.initials: X
authors.lastname: Guo
authors.forename: Dezhu
authors.initials: D
authors.lastname: Ma
mesh_terms: D002087:Butyrates / Q000737:chemistry*; D020148:Butyric Acid / Q000737:chemistry*; D006860:Hydrogen Bonding; D006880:Hydroxy Acids; D015394:Molecular Structure; D011422:Propionates / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: C509112:2,2-hydroxymethyl butanoic acid; D002087:Butyrates; D006880:Hydroxy Acids; D011422:Propionates; D020148:Butyric Acid; C110034:2,2-bis(hydroxymethyl)-propionic acid