Infrared Spectrum and UV-Induced Photochemistry of Matrix-Isolated Phenyl 1-Hydroxy-2-Naphthoate

The conformational stability, infrared spectrum, and photochemistry of phenyl 1-hydroxy-2-naphthoate (PHN) were studied by matrix isolation spectroscopy theoretical computations performed at the DFT(B3LYP)/6-311++G(d,p) level theory. main intramolecular interactions determining relative stability seven conformers molecule evaluated. According to calculations, twofold degenerated O–H···O=C intramolecularly hydrogen-bonded conformer with ring ester group ±68.8° out plane substituted naphtyl moiety is most stable molecule. This considerably more than second form (by ~15 kJ mol−1), in which a weaker O–H···O–C hydrogen bond exists. compound was isolated cryogenic argon N2 matrices, composition matrices investigated spectroscopy. In agreement predicted energies conformers, analysis spectra indicated that only PHN present as-deposited matrices. then irradiated various wavelengths narrowband tunable UV light within 331.7–235.0 nm wavelength range. resulted photodecarbonylation PHN, yielding 2-phenoxynaphthalen-1-ol, together CO. extension decarbonylation found depend on excitation wavelength.