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

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Presentation on theme: "CAITLIN BRAY CARA RAE RIVERA E. A. ARSENAULT DANIEL A. OBENCHAIN"— Presentation transcript:

1 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.

2 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

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

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

5 Comparison of Calculation and Experimental Results
Parameters g(d,p) Experimental A / MHz 3137.7(2) B / MHz (1) C / MHz (1) χaa / MHz 3.05(7) χbb - χcc / MHz 7.1187 [ ] DJ / kHz — 0.061(5) N 18 RMS / kHz 6.1 ∆E (cm-1) 322 15

6

7

8 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 G(d,p) basis set Ho Junming, Coote Michelle L,. WIREs Comput Mol Sci 2011, 1: doi: /wcms.43

9 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/ g(d,p)

10 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/ g(d,p)

11

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

13 Monomer hydroxyl stretch

14 Formic Acid Monomer hydroxyl stretch

15 Acetic Acid Monomer hydroxyl stretch

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

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

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