THE MICROWAVE STUDIES OF GUAIACOL (2-METHOXYPHENOL), ITS ISOTOPOLOGUES & VAN DER WAALS COMPLEXES Ranil M. Gurusinghe, Ashley Fox and Michael J. Tubergen,

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THE MICROWAVE STUDIES OF GUAIACOL (2-METHOXYPHENOL), ITS ISOTOPOLOGUES & VAN DER WAALS COMPLEXES Ranil M. Gurusinghe, Ashley Fox and Michael J. Tubergen, Department of Chemistry, Kent State University, Kent, Ohio

Motivation Intramolecular hydrogen bonding & conformational preferences Conformational changes upon forming van-der-Waals complexes :  Ar complex  Water complex GUAIACOL (2-METHOXYPHENOL)

Background Monomer2-aminoethanol-Ar 2-aminoethanol-water

Background Monomer Glycidol-Water

Guaiacol: Previous Ab initio Studies C. Agache and V. I. Popa, Monatsh. Chem. 137 (2006) 55-68

Previous Ab initio Studies global minimum kJ mol kJ mol -1 planar Non-planar Intramolecular H bond – kJ mol O. V. Dorofeeva, et al., J. Mol. Struct. 933 (2009)

Ab initio Studies MP2/ G(d,p) anti-synanti-antigauche-anti A / MHz B / MHz C / MHz µ a / D µ b / D µ c / D Relative Energy/kJ mol

Kent State FTMW Spectrometer Range : MHz Resolution : 2.4 kHz Carrier Gas :  He(30%)/Ne  Ar Temperature : 25 – 60 0 C Backing pressure : 1.5 atm Hydroxyl deuterated guaiacol prepared by stirring of guaiacol with D 2 O in 1:1 ratio for 48 hrs

Guaiacol Spectrum Experimental Results A/MHz (6) Δ K /kHz (3) B/MHz (2) δ J /kHz (1) C/MHz (1) δ K /kHz (1) Δ J /kHz (2) N 52 Δ JK /kHz (13) Δν rms Optimized anti-syn conformation Ab initio Results A / MHz B / MHz C / MHz

Spectroscopic Constants Normal 13 C(2) 13 C(3) 13 C(5) 13 C(7) 13 C( 8) 13 C(9) 13 C(14) 2 H(12) A/MHz (6) (5) (6) (4) (6) (7) (4) (9) (11) B/MHz (2) (3) (2) (4) (4) (4) (2) (4) (5) C/MHz (1) (1) (2) (2) (1) (1) (1) (2) (2) Δ J /kHz (2) (5) (2) (8) (7) (7) (4) (7) (8) Δ JK /kHz (13) (28) (14) (36) (3) (3) (19) (37) (41) Δ K /kHz (3) (7) (5) (80) (8) (9) (5) (7) (10) δ J /kHz (1) (2) (1) (4) (3) (3) (2) (3) (4) δ K /kHz (1) (3) (13) (6) (3) (3) (2) (4) (39) N Δν rms

Principal-Axis-System Coordinates of 13 C and 2 H from: Kraitchman Analysis & Ab-initio Method Isotopomer KraitchmanAb-initio | a| / Å| b| / Å| c| / Å a / Å b / Åc / Å 13 C(2) C(3) i C(5) i C(7) C(8) C(9) C(14) H(12)

Guaiacol-Ar: Ab Initio Studies MP2/ G(d,p) Structure Dipole Moments / DRotational Constants / MHz Relative E/ kJ mol -1 µaµa µbµb µcµc ABC Optimized Guaiacol-Ar complex 1 2 3

Guaiacol-Ar Spectrum Experimental Results A/MHz (14)Δ K /kHz (3) B/MHz (7)δ J /kHz (1) C/MHz (1)δ K /kHz (12) Δ J /kHz (3)N43 Δ JK /kH z (24)Δν rms Ab initio Results A / MHz B / MHz C / MHz

Principal-Axis-System Coordinates of Ar atom from: Kraitchman Analysis & Ab Initio Method More Ab-initio modeling need to be done for Guaiacol-Ar complex KraitchmanAb –Initio | a| / Å| b| / Å| c| / Å a / Å b / Åc / Å

Guaiacol-Water Complex Ab Initio Studies: MP2/ G(d,p) Structure Dipole Moments / D Rotational Constants / MHz Relative E/ kJ mol -1 µaµa µbµb µcµc ABC

Summary Ab initio calculations & rotational spectra for guaiacol, its isotopologues, Ar & water complexes Lowest energy conformation of guaiacol accommodates intramolecular hydrogen bonding Guaiacol-Ar : More modeling need to be done Guaiacol-Water : Work in progress

Acknowledgements Ohio Super Computer Center Kent State University, Kent, Ohio

Principal-Axis-System Coordinates of 13 C and 2 H from: Kraitchman Analysis & Ab-initio Method Isotopo mer KraitchmanAb-initio | a| / Å| b| / Å| c| / Å a / Å b / Åc / Å 13 C(2)2.2843(6)0.5690(26)0.0082(1828) C(3)1.4021(11)1.6485(9) I(-1020 i) C(5) I(-165i)1.4285(10)0.0249(601) C(7)0.4484(33)0.0885(169)0.0261(573) C(8)0.4142(36)0.9553(15)0.0075(1998) C(9)1.7929(8)0.7352(20)0.0226(663) C(14)2.7487(5)0.8002(18)0.0119(1255) H(12)1.0230(14)2.1655(6)0.0644(232)

Guaiacol-Ar models: Structures 1 & Å, 3.22 Å3.349 Å, Å 1212

Hydroxyl deuterated Guaiacol Preparation Rapid stirring of guaiacol with D 2 O in 1:1 ratio for 48 hrs Filtered out the organic layer Dried in a desiccator for another 48 hours Confirmed with NMR spectroscopy