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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


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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.