Structural and spectroscopic differences among the potassium 5-hydroxypentanoyltrifluoroborate salt and the furoyl and isonicotinoyl salts

Abstract FT-IR, FT-Raman and ultraviolet–visible spectroscopies were used to characterize the potassium 5-hydroxypentanoyltrifluoroborate salt (HTFB) while the theoretical structures of this salt in gas and aqueous solution phases were studied by using hybrid B3LYP/6-311++G** calculations and the self consistent reaction field (SCRF) and solvation (SM) models because these models consider the solvent effects. Good concordance were obtained among the predicted 1 H-, 13 C and 19 F-NMR chemical shifts for HTFB in aqueous solution with the corresponding experimental available data for this salt in CDCl 3 . The corrected solvation energy by using ZPVE and non electrostatic terms is higher for this salt (−103.73 kJ/mol) than those reported for furoyl (−84.72 kJ/mol) and isonicotinoyl (−95.05 kJ/mol). Evidently, the side chain in HTFB increase the solubility of this salt in water, as compared with furoyl and isonicotinoyl. The NBO analyses show that the potassium 2-isonicotinoyltrifluorborate salt in both media is most stable than hydroxypentanoyl and furoyl salts and, in particular, the side chain in HTFB generates a diminishing of its stability in aqueous solution. Probably, this low stability of HTFB in solution is due to the higher solvation energy and to the n→σ ∗ transitions no observed in the other salts. The AIM studies support the high stability of isonicotinoyl than the other two salts and, also, reveal the ionic characteristics of the K --O and K --F interactions observed in those three salts. The comparisons of the gap values for the three species suggest that the most reactive salt is isonicotinoyl while furoyl salt is the less reactive. The descriptors show the importance of study these salts in different media because the values in solution are slightly different in the three salts from those computed in gas phase. In addition, the harmonic force fields and the scaled internal force constants for the salt in both media are reported together to their complete vibrational assignments.