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IN MEMORIAM
PHILIP S. BAILEY
Philip S. Bailey, Professor Emeritus
of Chemistry, died on November 18, 1998, in Fort Worth, Texas,
at the age of 82. His wife, Jean, three children, and numerous
grandchildren and great-grandchildren survive him.
Phil joined the faculty of the
University of Texas at Austin in November 1945, and spent nearly
four decades as a member of the Department of Chemistry. From
his initial appointment as an assistant professor, he rose through
the academic ranks to become an associate professor in 1949 and
a full professor in 1957.
Phil's recruitment to the faculty
of the department was probably one of the fastest on record.
He inquired about the availability of a position here in early
September 1945, at which time he held a postdoctoral appointment
with R. P. Lutz (a person Phil often referred to as his “chemical
father”) at the University of Virginia. By mid-month he
had submitted a resum³ as requested by the then-chairman W. C.
Felsing. Phil was interviewed in late October, received an offer
by the end of the month, which he immediately accepted, and arrived
in Austin to start teaching on November 15th, at the princely
salary of $2,500 for nine months.
The record shows that Phil's expenses
for his interview trip amounted to a total of $142.98 and included
$115.08 for round-trip rail fare between Charlottesville, Virginia,
and Austin; $3.00 in tips to “four porters;” and $0.30
to check bags and coat in St. Louis. Attention to detail, as
reflected in the last two expenses, was one of Phil's premier
qualities. Despite the modest scale of his expenses, Phil ran
up against a problem that continues to plague visitors to the
university, namely paperwork and receipts. According to a letter
Phil received from Robbin C. Anderson, who had succeeded Felsing
as chair of the department, “I (Anderson) received the copy
of your expense account and regret to report that there is still
a bit of red tape. We are supposed to turn in a receipt for railroad
and pullman fare and any hotel bills. I am enclosing one of the
receipt blanks. The station agent at Charlottsville [sic] can
sign the receipt for you since the various railroad rates are
standard. If you will have this receipt signed and send it back
to me at once, I can have the check for you in a day or so thereafter
I believe.” What differs today from that time is the speed
with which Anderson thought he could get a check in the mail!
Prior to undertaking his postdoctoral
appointment, Phil earned a B.S. at Oklahoma Baptist University
(1937), where his father was a member of the chemistry faculty,
an M.S. (analytical) at the University of Oklahoma (1940), and
a Ph.D. (organic) at the University of Virginia (1944). The “Educational
Data” portion of his resum³ contained the following two
comments on his grades: At Oklahoma Baptist, Phil noted that
he had “mostly A's” in his chemistry courses but was “Average” in
his other subjects because “I had not `waked up' yet;” he
then reported that his grades in his first year at OU were “Poor” because “It
took me this year to wake up to what I wanted to do.” Suffice
it to say that Phil told it like it was.
Phil was the second of four consecutive
generations of chemists in the family, starting with his father
and continuing with two of his own children and then two grandchildren.
He himself was the consummate academician, loving the wonderful
combination of teaching, research, and service that the profession
engenders. Drawing from his teaching evaluations, which is always
a dangerous thing given the vagaries of students' opinions, one
can find the following quotes that capture the man: “I think
Dr. Bailey is extremely fair in his dealings with students, especially
with regard to exams. He is sincerely concerned with doing his
best in teaching.” “The material covered on the test
is so much that the student is mentally fatigued before
he is halfway through the tests.” (Phil was indeed thorough
on his examinations.) “Dr. Bailey has done a fine job of
teaching, and I, for one, appreciate his not making political
comments.” This opinion apparently was not shared by all,
as reflected in the following remark: [he] “was cold to
those who didn't agree with his political thoughts.” Indeed,
Phil held strong political opinions that sometimes were jokingly
characterized by two politically liberal colleagues, Professor
Roy Roberts and one of the co-authors (JCG) of this resolution,
as being somewhat to the right of those of Attila the Hun.
Phil's father started a family
tradition of performing chemical “magic” shows. This
was carried on by Phil himself, his son, Phil, Jr., and continues
with Phil's grandson Karl, and over 100,000 people have seen
the show over these four generations. Yet another family chemical
tradition in which Phil had great pride was membership in , the
fraternity for collegiate and professional chemists. He was a
founder of the chapter here, where Phil, Jr. was also a member.
Karl has maintained this tradition by joining the fraternity
as well.
Phil faced many personal challenges
during his tenure here at UT and always overcame them through
a combination of his strong religious faith and strength of character.
He had a fine sense of humor and loved to play practical jokes
on his colleagues, particularly Roy Roberts. Roy returned the
favor on numerous occasions, and he and a co-conspirator cooked
up one scenario that was truly memorable. It involved an alleged
edict from W. O. Milligan, the original Director of Research
of the Robert A. Welch Foundation, that all grant-holders were
to make a command appearance before him during one of his all-too-frequent
visits to the department. The two concocted a phony letter that
was shown to Phil the day after the supposed visit was
to occur, innocently inquiring as to why he hadn't shown up.
Phil nearly had a cardiac arrest as he envisioned his Welch grant
disappearing forever.
Although mild-mannered most of
the time, Phil did have a temper that was a sight to behold when
unleashed. Often his outbursts were triggered by his perception
that a principle that he held dear had been violated, but he
would usually calm down quickly and apologize to those he might
have verbally castigated. On one occasion Phil felt that his
anger might have been costly to him, as evidenced in a letter
he wrote to Chairman Bill Shive in 1965. Noting that he was unhappy
with the size of his raise for the ensuing academic year, Phil
said, “If the ... raise given me solely denotes a reprimand
for the unfortunate note which I, on the spur of the moment,
let go to the Dean's office several months ago, then I can understand
and am willing to take my punishment.” What the “unfortunate
note” contained is lost to history.
For many of his years on our faculty,
Phil served as Coordinator of the Organic Division and of the
sophomore-level organic courses. His dedication to both responsibilities
has set the standard for those who have followed him in these
positions. We all recall his unrelenting efforts to make the
health professions course in organic chemistry as rigorous as
the majors' and engineers' sections, and indeed he managed to
do so before relinquishing his duties as course coordinator.
Phil's contributions in research
at UT Austin ultimately earned him international recognition
in the field of ozonolysis of organic compounds, but his publishing
career began while he was still a graduate student at the University
of Virginia. His first paper, published in 1943 with his mentor,
Professor R. E. Lutz, and another co-author, C. E. McGinn, was
entitled “The Acylation of Beta-hydroxyfurans.” This
paper explored the interesting behavior of hydroxyfurans, especially
2,5-diphenyl-3-hydroxyfuran, as enols analogous to phenols. In
the ensuing five-year period, Phil published a total of twelve
papers with Professor Lutz, an enviable record for any graduate
student, even in the present-day context of prolific publication.
Many of these early projects involved other types of reactions
of furan systems and of their immediate precursors, 1,2-dibenzoylethylene
and 1,2-dibenzoylethane, but others included the synthesis of
phenethylamine type antimalarials, which was also a prominent
focus of the Lutz group at the time because of our involvement
in World War II.
Upon arriving in Austin in 1945,
Phil commenced his own research program, which naturally incorporated
many of the themes of the “Lutz chemistry” with which
he was so familiar. Once again, 1,2-dibenzoylalkenes were a favorite
target for study, especially the reactions of these molecules
with amines, halogens, alcohols, and a variety of other reactants.
To the twelve papers he published as a co-author with his “chemical
father,” Phil added twenty-three more in subject areas related
to or inspired by this earlier chemistry. Then after building
his career for ten years, Phil made the bold decision, brilliant
as it turned out, to study and work in the laboratories of Professor
R. Criegee at Karlsruhe, Germany, where he first became familiar
with the exciting field of ozone chemistry. His tenure there
in 1953-1954 as a Fulbright Scholar was highly productive, leading
very quickly to two individually authored papers in Chemische
Berichte in 1954 and 1955. These papers where entitled, respectively, “Nùtiz Ùber
die Ozonisierung von Camphen” and “ ber die Ozonisierung
von Camphen.” The year in Karlsruhe was definitive for the
development of Phil's future research direction, for he would
devote himself singularly to this subject for the remainder of
his long scientific career.
The unusually high reactivity of
ozone, a rather simple molecule, translates into an ability to
react with virtually any organic molecule known. Further, the
correspondingly low selectivity of ozone often results in an
array of competing reactions and mechanisms and in secondary
and tertiary reactions, all of which serve to favor the formation
of complex product mixtures. Finally, the relative cheapness
of this common chemical, which is readily made from oxygen, its
ability to purify water, and the novel peroxidic nature of the
products of its reactions combine to present an attractive and
challenging field of investigation for any investigator. It was
into this rich and diverse field of research that Phil and his
students plunged in the mid-1950s.
Phil's group energetically pursued
a wide variety of reactions of ozone with organic molecules,
virtually always with the intention of elucidating a deeper mechanistic
understanding of these reactions. Predictably, some of the early
investigations involved the reactions of ozone with 1,2-dibenzoylalkenes
and furans, but Phil's attention soon turned to the reactions
of ozone with aromatic compounds. Much of the previous attention
to ozone in organic chemistry had focused on its reactions with
alkenes to ultimately cleave the carbon-carbon double bond. However,
ozone is sufficiently reactive even to cleave aromatic bonds,
and this field was especially attractive to Phil. He established
that ozone reacts selectively at the 1,2-bond of naphthalene
and at the 9,10-bond of phenanthrene in a way much like the corresponding
reactions with alkenes. The reaction with phenanthrene turned
out to be especially interesting in that it smoothly produces
diphenic acid, a reaction that became the centerpiece for two
patents. The mechanistic diversity of ozone, however, began to
become apparent in the studies of the Bailey group on the ozonation
of anthracene. Three different types of reaction were discerned:
a typical reaction across the 1,2-bond, a stepwise (presumably
electrophilic) reaction at C-9, and a conjugate addition across
the 9,10-bond. The latter was unprecedented, representing a theoretically
forbidden [4+4] cycloaddition.
Having contributed extensively
to our basic understanding of the mechanisms of ozone's reactions
with aromatics, Phil then increasingly focused on its classic
reaction with alkenes, and specifically on achieving a more refined
mechanistic understanding of these reactions. The basic Criegee
mechanism for the ozonolysis of alkenes had been developed in
the 1949-1953 time frame, primarily in Professor Criegee's laboratory.
However, a number of observations that seemed to be inconsistent
with this basic mechanism eventually appeared in the literature.
These reports culminated in a 1967 paper in which Murray, Youssefyeh,
and Story concluded that the Criegee mechanism was incorrect
and proposed a distinctly different mechanism for the unusual
ozonolysis data obtained by themselves and others. By recognizing
that the apparently anomalous results could be readily explained
if the existence of syn- and anti-zwitterions is
acknowledged, Bailey and another of the authors of this resolution
(NLB) were able not only to defend his mentor's (Criegee) mechanism
successfully but also to furnish many further mechanistic insights
into this reaction. A major focus of the Bailey group's research
from that time on became the experimental substantiation of this
elaborated version of the Criegee mechanism.
Phil published well over 100 research
papers, as well as numerous book chapters, a Chemical Reviews
article, and three patents in the course of his productive career,
and his contributions are such that his influence on the field
of ozone chemistry today cannot be overestimated. Nonetheless,
the crowning achievement of his scientific career was not engendered
in the aforementioned publications: During a large portion of
his last ten years as an active researcher, Phil's consuming
passion was to write the definitive treatise on ozone chemistry,
and he achieved this lofty goal. The second and final volume
of this two-volume opus entitled “Ozone in Organic Chemistry” was
published in 1982, just five years after the first volume appeared.
Phil opted to retire in his mid-sixties,
but planned to continue teaching on a one-half time basis. He
served in this part-time status for only one year, realizing
that he had better things to do than to spend over an hour each
day traveling between Lago Vista, where he had a home on Lake
Travis, and the campus. In the letter he wrote to Chairman Mike
White in October 1983, he cited several reasons for taking full
retirement: “... Second, I feel that I have accomplished
all that I am capable of in a significant fashion in research.
[My investigations of ozone-organic chemistry have] culminated
in my two volume treatise published by Academic Press. ... These
volumes are now considered the authoritative standard works in
the field. In addition, I have to show for my 39 years [at UT
Austin] well over 100 research publications. I feel, however,
that the significant advances in the ozonation field will, in
the future, come primarily from the theorists and those capable
of working at extremely low temperatures. ... Fourth, I have
many other interests I want to spend more time with. These include
learning more about other sciences and disciplines, writing scientific
papers of a more popular nature, working around my home, boating,
photography, etc.” As reflected in his own words, Phil was
a man who knew himself and acted on that understanding.
Phil Bailey symbolized the best
one finds in an academic colleague, and his influence was important
to the evolution of the Department of Chemistry and Biochemistry.
He is no longer with us, and we are all the lesser for his absence.
<signed>
Larry R. Faulkner, President
The University of Texas at Austin
<signed>
John R. Durbin, Secretary
The General Faculty
This Memorial Resolution was prepared by a special committee consisting of Professors
John C. Gilbert (Chair), Nathan L. Bauld, and Gerhard J. Fonken.
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