CAITLIN BRAY CARA RAE RIVERA E. A. ARSENAULT DANIEL A. OBENCHAIN

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Presentation transcript:

HYDROGEN BONDING IN 4-AMINOPHENYL ETHANOL: A COMBINED IR-UV DOUBLE RESONANCE AND MICROWAVE STUDY CAITLIN BRAY CARA RAE RIVERA E. A. ARSENAULT DANIEL A. OBENCHAIN STEWART E. NOVICK JOSEPH L. KNEE Department of Chemistry, Wesleyan University, Middletown, CT, USA.

Resonance Spectroscopy Methods Fix probe 355nm Scan pump 4-AE+ + e- Pump Energy ( cm-1) Ionization Signal I.P. S1 S0 Resonance Enhanced Multi-Photon Ionization IR-UV Double Resonance Spectroscopy 4-AE+ + e- Fix pump Scan IR S1 I.P. S0

Chirp Pulse Microwave Experiment Chirped pulsed FTMW spectrometer was utilized to obtain the rotational spectra of 4-aminophenyl ethanol in the 9-12 GHz range Heated nozzle 95˚C (m.p. of 4-aminophenyl ethanol is 107-110˚C) 0.9-1.1 atm dry argon flowed 120,000 averages

4AE Monomer Two conformations with an energy difference of ~320 cm-1 Gauche side view Anti 320 cm-1 Gauche 0 cm-1 rb3lyp/6-311++g(d,p)

Comparison of Calculation and Experimental Results Parameters 6-311++g(d,p) Experimental A / MHz 3132.7374 4218.7441 3134.3508 3137.7(2) B / MHz 736.59983 600.77004 736.08033 735.057(1) C / MHz 690.69620 557.81326 691.01854 680.158(1) χaa / MHz 2.73007 2.77791 1.09797 3.05(7) χbb - χcc / MHz 5.87472 7.1187 4.57268 [5.87472] DJ / kHz — 0.061(5) N 18 RMS / kHz 6.1 ∆E (cm-1) 322 15

Acids Studied Acid Structure pKa Gas Phase Acidity (kcal/mol) Mass Formic 3.75 338.6 46 Acetic 4.76 341.5 60 Propionic 4.88 340.4 72 HA(g) → H+(g) + A-(g) DG = Gas Phase Acidity - smaller DG for Stronger Acids * DFT calculation using B971 Functional with 6311-++ G(d,p) basis set Ho Junming, Coote Michelle L,. WIREs Comput Mol Sci 2011, 1: 649-660. doi: 10.1002/wcms.43

4AE Gauche (towards ring) -3527 Conformation Structure Energy (cm-1) Binding Energy (cm-1) 4AE Gauche (towards ring) -3527 4AE Gauche 170 -3357 4AE Anti 188 -3662 4AE Gauche bound to NH2 309 -3219 4AE Anti bound to NH2 556 -3293 *Calculated using rb3lyp/6-311++g(d,p)

Acid Clusters All same lowest energy structure Hydrogen bonding distances about the same Formic Acid Bond lengths: 1.7 and 2.5 O-H bond Note that the bond length between H on hydroxyl and on the ring switches to hydroxyl H 3.3 Acetic Acid Propionic Acid rb3lyp/6-311++g(d,p)

From 9FCA work and –OH stretches 9-flourenecarboxylic acid Scaling factor 0.952 From 9FCA work and –OH stretches rb3lyp/6-311++g(d,p)

Monomer hydroxyl stretch

Formic Acid Monomer hydroxyl stretch

Acetic Acid Monomer hydroxyl stretch

Wrap up Propionic acid? Second conformation Hydrogen bonding from the perspective of a “base”

Acknowledgments Wesleyan University Joseph Knee Cara Savino Dan Obenchain, Eric Arsenault, Steve Cooke, and Stewart Novick DoD SMART program