Transcript Fun, Foibles, and Follies In Collaborative Research

Fun, Foibles, and Follies In
Collaborative Research
Bruce A. Hathaway
ACS Southern Illinois
Local Section Meeting
February 7, 2000
Foible, According to Webster
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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
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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
H
H
COOH
O
COOH
HOOC
Pyridine, reflux
R
H
R
COOH
H 2SO4 or
PPA
H2/Pd
n-BuONO
R
R
O
OH
N
R
O
NH2
H2/Pd,
HOAc, 60o
NH2
R
Amphetamine
55° “Hot-Plate” Latency,
5 mg/kg
14
12
10
8
6
Sec.
4
2
0
Saline
2-AI
Me
Et
iProp
Bu
iBu
tBu
Mouse Spontaneous Motor
Activity Meter
Computer
8 Photocells
Mouse Spontaneous Motor
Activity, 5 mg/kg
700
600
500
400
300
200
100
Counts
Per 30
Min
0
Saline
2AI
Me
Et
iprop
Bu
ibu
t-bu
2-Aminoindane Conclusions
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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 NonLinear Optical (NLO) Materials
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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
2 R C
R'
R C
C
C
C
C
H + Br C
Air, Cu+1
amine
solvent
H
H
C
R C
C
Br2, NaOH or
R'
AgNO3
N-Bromosuccinimide
R'
(Ph3P)2PdCl2, CuI
Et3N solvent
C C
C
C
R C
R
Br
C
C C
R'
Preparation of “DAMNA”
HOCH2
C
C
H
CH3
CH3
F
C
CH3
C
CH
C
Br
CH3
C
CH
O2N
CH3
Br C
C
N
CH3
N
O2N
H
N
HOCH2
CH
K2CO3
O2N
CH3
Br2, NaOH
C CH2OH
(Ph3P)2PdCl2, CuI
Et3N solvent
O2N
CH3
N
C
C C
"DAMNA"
C
CH2OH
Polymerization of Diacetylenes
R C C C C R
R C C C C R
R C C C C R
UV light
R C C C C R
R C C C C R
R C C C C R
Diacetylenes
Polydiacetylene
NASA-JOVE “Good News”
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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”
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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
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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
H
H
H2N
O
N
O
N
P OEt
OEt
C
R1
G1
G1
G2
R2
1. NaH
N
G2
2.
N
R2
Azines
R1
O
G1
N
R1
O
P OEt
OEt
Glaser Results
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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.
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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
HO
SnCl4,
R
HO
HO
C
C
O
C
O
R
H
C
H
O
C
1. SOCl2
2. Et3N or heat
C
R
Arylphenylketene
Preparations of Ketenes
2
R
HO
H C
HO
O
HO
C
OH
C
O
C
H2SO4, HOAc
R
H
R
O
C
1. SOCl2
2. Et3N or heat
C
R
Diarylketene
R
Ketene Results
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Seven different ketenes have been
prepared.
Some ketene complexes have been
prepared.
At least one presentation will be made
this year.
Acknowledgements
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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.