Fun, Foibles, and Follies In Collaborative Research Bruce A. Hathaway ACS Southern Illinois Local Section Meeting February 7, 2000
Jan 09, 2016
Fun, Foibles, and Follies In Collaborative
Research
Bruce A. HathawayACS Southern IllinoisLocal Section Meeting
February 7, 2000
Foible, According to Webster The part of a sword blade between
the middle and the point. A minor flaw or shortcoming in
personal character or behavior. An eccentric or whimsical liking or
interest in something.
Introduction
Collaborative research, to me, is where two or more individuals work together on a project. Each individual has defined responsibilities, and shares the credit, glory, honor, and (heaven-forbid) blame for the results. Ideally, the collaborators should work as equals, and have input on the planning, direction, and dissemination of the results. In this presentation, I will share some of the collaborative projects I have been involved with, including how the collaboration was initiated, the nature of the collaboration, and the good and bad points of the collaborations.
2-Aminoindanes with Steve Overmann 1984-89 Students got us together (Archie
Thurston and Rick Tolan). 6 students involved: Two went on and
obtained Ph.D.’s (Archie Thurston and Chip Wittenbrink).
I supervised preparations, Steve supervised biological evaluation.
Mike Rodgers did computer interfacing.
Synthesis of 2-Aminoindanes
R
H
O
R
H
COOH
H
COOH
HOOC
Pyridine, reflux
H2/Pd
R
COOH
RO
RO
N
OH
R
NH2H2/Pd,
HOAc, 60o
n-BuONOH2SO4 orPPA
NH2
Amphetamine
55° “Hot-Plate” Latency,5 mg/kg
0
2
4
6
8
10
12
14
Saline 2-AI Me Et iProp Bu iBu tBu
Sec.
Mouse Spontaneous Motor Activity Meter
8 Photocells
Computer
Mouse Spontaneous Motor Activity, 5 mg/kg
0
100
200
300
400
500
600
700
Saline 2AI Me Et iprop Bu ibu t-buCountsPer 30Min
2-Aminoindane Conclusions No “really good” compounds were
discovered. We couldn’t obtain external funding. No publications Steve became more interested in other
research projects. 6 presentations at MAS, other
meetings. 2 GRFC grants.
NASA-JOVE: Preparation of Non-Linear Optical (NLO) Materials 1993-8 NASA invited Southeast to participate. I had to find a NASA colleague to work
with. Spent one summer at Marshall Space Flight
Center and the Univ. Alabama - Huntsville in Huntsville, AL.
6 students involved (Jennifer Mabery, Jamie Carrigan, Angela Scates, Pat Zimmermann, Brian Taylor, Jeremy Wittenborn).
Preparations of Diacetylenes
C CR H CC R'Br+ R'CCCCR(Ph3P)2PdCl2, CuIEt3N solvent
C CR H2 Air, Cu+1
aminesolvent
RCCCCR
C CR' HBr2, NaOH orAgNO3
N-Bromosuccinimide
C CR' Br
Preparation of “DAMNA”
C CHOCH2 HBr2, NaOH
C CHOCH2 Br
CH3
F
O2N
NH
CH3
CCH
K2CO3
CH3
N
O2N
CH3
C CH
CH3
N
O2N
CH3
C CHCC CH2OHBr
(Ph3P)2PdCl2, CuIEt3N solvent
CH3
N
O2N
CH3
C C C C CH2OH
"DAMNA"
Polymerization of Diacetylenes
R C C C C R
R C C C C R
R C C C C R
R C C C C R
R C C C C R
R C C C C R
UV light
Diacetylenes Polydiacetylene
NASA-JOVE “Good News” Money for summer salary, student
workers, travel, operations. Summer JOVE meetings in Texas,
Florida, and California. Three publications and several
presentations by my students and I from the work we did.
Led to further collaboration.
NASA-JOVE “Bad News” My collaborator was only interested
in his compound, “DAMNA”, and did little with 25 we made.
He only contacted me when he wanted me to make more of his compound.
He never made me a co-author on any of his publications, nor acknowledged the work I did.
Rainer Glaser: NLO Materials 1997 - present We met at Organic Chemistry Day
at University of Missouri, when I presented a poster on NASA-JOVE research.
I prepare NLO materials, and Glaser gets X-ray structures and does theoretical calculations.
Preparations of Azines as NLO Materials
C
N
R1
N
H
P
OEt
O
OEt
G1G1
O
R1
H2NN
H
P
O
OEtOEt
1. NaH
2. G2
O
R2
G1
N
R1
G2
N
R2
Azines
Glaser Results Two publications and one
presentation. I received an ACS-PRF grant for my
part of the research. Four students have been involved
(Gary Bohnert, Scott Kirkley, Rachel Phillips, Steve Updike), one who is in the Ph.D. program at Missouri (Gary Bohnert).
Preparations of Ketenes with Jin Gong. Begun seriously in 1999 (some
informal consulting earlier). I supervise preparation of ketenes,
and Jin’s students react them with transition metal complexes.
Jin pays for one student (Andy Gilbert) whom I supervise.
Preparations of Ketenes
SnCl4,
C
C
HO
HO O
H
R C
CHO O
HR
C
C
O
R
Arylphenylketene 1. SOCl22. Et3N or heat
Preparations of Ketenes
R C
CHO O
HR
C
C
O
R
Diarylketene 1. SOCl22. Et3N or heat
C C
HO
HO O
OH
H
2H2SO4, HOAc R
R
Ketene Results Seven different ketenes have been
prepared. Some ketene complexes have
been prepared. At least one presentation will be
made this year.
Acknowledgements All of the undergraduate students
who did most of the work. Funding by NASA, ACS-PRF, GRFC,
and the Southeast Chemistry Department.
Helpful conversations with Southeast faculty, especially Bjorn Olesen.