Volume 92 Issue 33 | pp. 26-27
Issue Date: August 18, 2014 | Web Date: August 17, 2014

Reflections On ChemDraw

Recalling the origins of the beloved structure-drawing program as its 30th anniversary approaches
Department: Science & Technology
Keywords: ChemDraw, Cambridge Scientific Computing, CambridgeSoft, Dave Evans, Sally Evans, Stewart Rubenstein, Perkin Elmer

ChemDraw, the software program used by chemists worldwide to draw molecular structures, was invented to save Dave and Sally Evans’s marriage. Or at least that’s how Harvard University chemistry professor David A. Evans tells the tale of the software’s origins in a recent essay in Angewandte Chemie (DOI: 10.1002/anie.201405820).

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QUICKDRAW
Caffeine is a snap to illustrate with the latest version of ChemDraw.
Credit: C&EN
A ChemDraw screengrab.
 
QUICKDRAW
Caffeine is a snap to illustrate with the latest version of ChemDraw.
Credit: C&EN

In 1983, Evans moved his laboratory from California Institute of Technology to Harvard. His wife, Sally, had to leave her job teaching science and math at the Westlake School for Girls in Holmby Hills, Calif., where students were often the daughters of celebrities, such as movie icon Gregory Peck, and comedians Richard Pryor and Carol Burnett. Some students even became celebrities themselves, including astronaut Sally Ride and actress Bridget Fonda.

Dave and Sally Evans arrived in Massachusetts in the autumn of 1983, and it was too late for Sally to look for a teaching job. So she agreed to help Dave set up his new lab space, effectively becoming the lab’s manager.

Many of the job’s responsibilities were rewarding, she recalls, such as working with an architect to design the new lab space and designing a brochure for the Harvard chemistry department. But if there was one responsibility she found trying, it was the tiresome task of drawing chemical structures. She would sit at a drafting table for up to four hours at a time using drafting tools, stencils, and rub-off letters to create the chemical structures that would be incorporated into her husband’s lecture slides and publications.

Chemists who completed their studies before the advent of structure-drawing software will surely recall the tedium of chemical structure drawing. “For my thesis, which was written in 1980, I learned how to be a draftsman,” says Scott E. Denmark, a chemistry professor at the University of Illinois, Urbana-Champaign. “During the early stages of my career, from 1980 to 1985, all of the schemes for my publications and the artwork for my lectures, which were turned into slides, were all hand drafted. If you drew a scheme and you realized you made a mistake, you’d have to erase the whole thing,” he says, using a special eraser that resembled a dentist’s drill. “You can imagine how long it took,” he says.

“If you smudged the ink, you had to start all over,” Sally Evans says. “I’d draw a fairly complex molecule and Dave would change one functional group, and I’d have to draw the whole thing over again.”

Venting her frustration one afternoon in early 1985, Sally turned to graduate student Stewart Rubenstein and asked: “How would you like to save my marriage?”

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OLD SCHOOL
Before ChemDraw, chemists relied on tools such as this chemist’s triangle, developed by Harvard chemist Louis F. Fieser, for structure drawing.
Credit: Linda Wang/C&EN
A Chemist's Triangle, which was once used by chemists to draw structures before the advent of computer graphics programs.
 
OLD SCHOOL
Before ChemDraw, chemists relied on tools such as this chemist’s triangle, developed by Harvard chemist Louis F. Fieser, for structure drawing.
Credit: Linda Wang/C&EN

At the time, Rubenstein was working in E. J. Corey’s group on a computer-aided synthesis project known as LHASA, short for Logic & Heuristics Applied to Synthetic Analysis. Rubenstein had come to Harvard after doing undergraduate studies in chemistry at Stanford University, where he became interested in the interface between computer science and chemistry. He had picked up his programming skills as a high school student in Thailand, where his father worked for a few years as a chemical engineer. Rubenstein recalls working on an IBM mainframe owned by a classmate’s father’s company. He would use the computer at night after the payroll had been processed.

Rubenstein and Sally Evans had become friendly, talking with each other about their recently purchased Macintosh computers. “The Macintosh was really the first computer that could do decent graphics,” Rubenstein recalls. He decided that he had to have one and bought a Mac out of his own pocket in late 1984.

Dave and Sally Evans had likewise bought a Mac in early 1985. “The first night we had it, I looked at the graphics program MacDraw and I said to Sally, ‘This program would not be hard to modify for drawing structures,’” Dave Evans remembers.

In addition to saving the Evanses’ marriage, Rubenstein had his own motivation for developing a structure-drawing program: “I was going to have to write a thesis that had hundreds of chemical structures in it,” he says.

From there, ChemDraw began to evolve. “I just started writing the software and Dave and Sally started giving me feedback, and then Dave’s students started giving me feedback,” Rubenstein remembers.

Sally Evans recalls one particular day when Rubenstein came to her excited about a hexagon-drawing tool he’d come up with. “He could click the mouse on it and make it any size. And I said, ‘No, I want them all the same size,’ ” she says, knowing that chemists would want standard rings, bond lengths, and bond angles.

The program developed little by little in this manner, with Sally channeling the needs of chemists and Rubenstein doing the programming. In July of 1985, ChemDraw premiered at the Gordon Research Conference on Reactions & Processes in New Hampshire. Rubenstein and the Evanses demonstrated it during a break in the conference. Bad weather kept the conferees indoors, so attendance was high.

Stuart L. Schreiber, then a chemistry professor at Yale University, saw the demo and recalls “knowing instantly that my prized drafting board and my obsessive drafting of chemical formulas were over.”

Schreiber holds the distinction of being the first person to purchase ChemDraw. “The impact of seeing ChemDraw on a Macintosh computer was dramatic and immediate,” he says. “There was no doubt that this was going to change the way chemists interact with each other and the rest of the scientific community,” he says. At the time Schreiber was proudly using his Xerox Memorywriter electronic typewriter with two lines of editable text. “The combination of the Macintosh computer and ChemDraw clearly demanded next-day adoption.” He rushed home to New Haven and placed his order.

Rubenstein says he picked the software’s pricepoint—$295 for academics and $495 for industrial users—by asking what was the maximum amount users could purchase without getting approval from their institutions and then subtracting $5.00.

Word of ChemDraw spread primarily via Dave Evans that first year. “He would give these lectures with slide after slide of these beautiful structures,” Rubenstein says. Then on the last slide, alongside thanks to the funding agencies, graduate students, and postdocs, he would also thank Rubenstein for writing ChemDraw, the program that created his structures, and he’d include Rubenstein’s phone number. “That’s how I started getting calls from people asking how they could get a copy of the program,” Rubenstein says.

“Writing the program was no big deal. If we hadn’t done it, in a few years somebody would have done it,” Dave Evans says. “The reason why this program was so quickly received was because I really insisted on it meeting my standards, and I’m really picky about these sorts of things. The quality was at the right level when it was introduced. We also did a very good job with beta testing so that when people started working with the program it wasn’t continually crashing.”

Homer Pearce, a scientist at Eli Lilly & Co. in the mid-1980s, recalls standing over Evans’s shoulder as he demonstrated the software in an office at the pharmaceutical company for the first time in 1985. “I was amazed at how intuitive the program was, and I was amazed at the beautiful pictures of chemical structures it produced,” he says. “It was just so easy to input structures and get pretty results that were appropriate for lots of different formats, such as publications or communication.

“Within two years of Evans’s visit, every chemistry laboratory at Eli Lilly had a Macintosh running ChemDraw. It definitely changed the way we thought about presenting ideas. The ability to go into a detailed description of a synthetic scheme and keep structures in the computer database that could be called up for future reference really became quite profound,” Pearce says.

Rubenstein is more circumspect about the mark he’s made on the chemical enterprise. “I was at the right place at the right time with the right expertise,” he says. “Dave told me that my biggest contribution to chemistry was making certain famous chemists’ structures legible.”

ChemDraw’s success eventually prompted Rubenstein to leave graduate school. Sally Evans helped set him up with a lawyer, and in 1986 Cambridge Scientific Computing, which would eventually become CambridgeSoft, was launched.

Rubenstein says for several years he continued to pay registration fees at Harvard thinking he’d go back to finish his degree. “I actually tried to sell off ChemDraw to a publisher,” he says, but it didn’t work out.

Rubenstein soon recruited his brother Michael, who had recently graduated from Oberlin College with a theater arts major and computer science minor, to answer the phone and help develop the software. The company began to grow from there. With each successive version came new features, many of which developed from customer requests, says Michael J. McManus, who was the fifth employee at CambridgeSoft and worked there for 10 years.

“Stewart was very receptive to feedback,” McManus says. “The product has become what it is today because of those enthusiastic users and because the company was receptive to hearing that input.” Also, he says, other chemical drawing software that was around at the time, such as Chem­Intosh, gave the company some needed competition. By the time it was sold to PerkinElmer in 2011, CambridgeSoft had scores of employees and a sizable office in Cambridge, Mass.

Today ChemDraw is the most popular chemical structure drawing software available. Over a million people use it worldwide, and not just on Macs any more, according to Hans Keil, PerkinElmer’s chief information officer. A Windows version was unveiled in 1994. The latest version, ChemBioDraw 14, launched earlier this year, offering direct searching with SciFinder, a product of the American Chemical Society’s Chemical Abstracts Service. There is also a mobile version that can be used on iPads.

Stewart Rubenstein retired from CambridgeSoft in 2006. These days he plays tournament bridge, traveling to competitions across the country. Sally Evans eventually returned to teaching. Dave Evans has shut down operations in his Harvard laboratories, but he continues to write scholarly papers and essays. He and Sally are still married. They’ll celebrate their 52nd wedding anniversary in December.  


Dear Reader

After reading this article, please let us know what you think. Responses to the survey questions will appear below soon.


Jump to responses:
Do you recall your experience drawing chemical structures before ChemDraw
or your early adventures with program?


Bruce Hathaway

In the mid 80's, we had purchased an Atari home computer, that I used to write exams, but had to hand draw all of the chemical structures. I found a program (I don't remember the name) that remapped the keyboard so I could draw chemical structures, somewhat crudely, until I bought a Macintosh and Chemintosh in the early nineties.

Dylan Bleier

Drawing large 3D organic molecules without ChemDraw is brutal and slow.

Robert Topper

I was one of the graduate students at Yale that benefited from Stu Schreiber's early buyin to ChemDraw. There was a copy which could be used at a common terminal, a Mac Plus, in the NMR lab, with even (gasp) a *laser printer.* As a physical chemist, ChemDraw might not seem all that essential to me - but its arrow templates were a huge boon. I was able to use CD to make complex chemical reaction kinetics schemes, and my first contribution to the literature was a scheme I made for a paper by Nelson DeLeon and Clay Marston (J. Chem. Phys. 91, 3405 (1989)). Thanks, ChemDraw!

Nick Greeves

I've used Chem(Bio)Draw since 1988 coauthoring two editions of a textbook on Organic Chemistry and a website ChemTube3D http://www.chemtube3d.com using the software. I was also a beta tester for many years. I can recall the use of Rotring pens and Letraset but I prefer using my Macs to produce vector graphics. Thanks Stewart and CambridgeSoft!

Bruce Hathaway

In the mid 80's, we had purchased an Atari home computer, that I used to write exams, but had to hand draw all of the chemical structures. I found a program (I don't remember the name) that remapped the keyboard so I could draw chemical structures, somewhat crudely, until I bought a Macintosh and Chemintosh in the early nineties.

Sanjay Batra

Drawing the chemical structures before we started using ChemDraw was little cumbersome. Being good in arts and drawing I quickly learnt the art of drawing the chemical structures using the templates and Stredler pen. Although placing the structures symmetrically was an issue I resolved it by placing two templates perpendicular to each other. The bigger problem arose when the structures were to be incorporated in the thesis because their placement required appropriate space in a document being typed on electronic typewriter. As there were little option to resize the structures we either drew the structure sitting next to the typist or saw to it that all schemes were placed on a separate page. Slide making was also difficult as the option to color them as per the requirement was not possible. How cheers to ChemDraw as all these issues are things of past now

Ganesan Vaidyanathan

Yes, some time using draftsmen and then with rub off stencils sold by Aldrich, which is what I used for my Ph.D. Thesis. What a long way we have come. ChemDraw was an integral part of the work we did and continues to be.

David Nehrkorn

Yes I do! I used Version 1 on my Mac in the mid 80's. Before ChemDraw, there was no suitable application. For my Ph.D. thesis, finished in 1974, I had a friend of mine who was a graphic artist draw the structures.

William Feld

As a student in J.K. Stille's group in the mid 60's, I made a lot of cash drawing structures for many theses. I used KOH-I-NOOR Rapidograph pens and lettering set (still available) and a plastic template that had various shapes cut into it. Later, I used a template designed by D. Seyferth and distributed by Alpha/Ventron. All of these templates had to have a set of spacers connected to the back of them to keep ink from the pens from running under the template. The advent of computer based drawing programs changed a lot but still do not prevent strange choices of fonts, spacing and placement on pages.

Robert Buntrock

Educated in the late '50s and mid '60s, structures for "finished" work or theses were drawn with hetero atoms typed in. Fortunately Princeton then allowed theses to be photocopied from typed manuscripts which made life easier for my wife (who typed my thesis) and I. We used additional stencils with a wider variety of polygons than Fieser's template. My need for drawing structures dropped off rapidly when I regretfully left the lab but I welcomed the excellent package from STNExpress, good for searching CA on STN (which I didn't have to do that often since I typically searched "simpler" molecules. I have an aged version of ChemDraw (from a review of CS ChemOffice) which I should update.

Donald Boyd

ChemDraw played a pivotal role in changing the negative attitude many bench chemists had toward computers in the 1980s. See "How Computational Chemistry Became Important in the Pharmaceutical Industry," Reviews in Computational Chemistry, Wiley-VCH, 2007, Vol. 23, pp. 401-451.

Lloyd Goding

I still have my 'Fieser triangle'; I keep it with my sliderule.

Richard Laursen

Dave Evans is quoted as saying, “Writing the program was no big deal. If we hadn’t done it, in a few years somebody would have done it.” It would have been less than a few years. In early 1985 one of my graduate students, Hann-Bin Chuang, at Boston University, developed and copyrighted a similar program, which he called CSD2D, using a DEC PDP-11 (I think). He used this program to write his own Ph.D. thesis. He also interfaced the computer with various instruments to produce computer-generated spectra for his thesis. All this is routine these days, but it was not then.

Katherine Flynn

I believe a group of us in the Agricultural Chemicals Division at Rohm & Haas in Springhouse, PA in the mid-1980's simply got together at lunch one day and drew up a proposal to purchase a MAC and ChemDraw as a common use computer and program for all. Of course, it was immediately useful and popular. What simple days before complicated IT processes to evaluate new software!

Glenn Howes

After Stu retired, I was responsible for keeping ChemBioDraw running on Mac at CambridgeSoft for several years. One thing about ChemDraw users. They are perfectionists and will notice if an atom label is a pixel to the right or if a bond truncated wrong.

Tom Zebovitz

ChemDraw was the procrastinator's friend. Minutes before I was scheduled to present my research at group meeting, I'd be on my first gen Mac, dashing off the appropriate structures. Often I could modify a talk I'd given earlier, since usually, not a ton happened over the past two weeks. The only bugaboo was that the older Mac I was using, mainly because I was one of the newer employees at my company, was very slow, and if I hit a certain key, the thing would redraw the screen excruciatingly slowly.

Ratna surya alwi

As a Ph.D student in material science, kanazawa univ. Japan. I used ChemDraw for made a paper and for a Ph.D. Thesis. Drawing organic structure without ChemDraw was complicated and too slow. Thanks ChemDraw,Stewart and CambridgeSoft!

Ratna surya alwi

As a Ph.D student in material science, Kanazawa Univ. Japan. I used ChemDraw for a paper and for a Ph.D. Thesis. Drawing organic structure without ChemDraw was complicated and too slow. Thanks ChemDraw, Stewart and CambridgeSoft!

 
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Comments
William Wordsworth (Wed Aug 20 12:18:57 EDT 2014)
I´ve still got my Fieser's Chemist's Triangle (also green!) somewhere in storage. I last used it when typing up my final year undergraduate project (Sept-1989 to June 1990) on an Amstrad PC. I typed all the text, left enough space to draw the structures later, printed the pages on my dot matrix printer, and then used the triangle to fill-in the reaction schemes etc.

When I started my PhD in October 1990 - the department acquired an Apple Mac LC - together with ChemDraw! It was different world altogether! Never looked back! been using ChemDraw ever since. And yes, I STILL call it ChemDraw! :-)
Vanessa (Tue Jun 16 13:13:17 EDT 2015)
Celebrate 30 years of ChemDraw with the creators on June 25th in Cambridge, MA. Register here http://bit.ly/1zNjays
Steven Steindel PhD FACMI (Mon Sep 01 10:50:38 EDT 2014)
I got my PhD in Natural Products Chemistry from Ga Tech in 1973. You can be assured that my fluency with organic drawing templates was profound, given the number of redraws! In 1973 I started a Postdoc with Michael Rossmann at Purdue and was assigned to the structure determination team for LDH. In 1974 Drs. Holbrook, Liljas and Rossmann were asked to produce an article in Dr. Boyer’s series “The Enzyme”. I was asked to participate and was assigned the figures and tables. The final article contained 34 figures and 24 tables. Dr. Holbrook provided many of the biochemical reactions and tables from his work while we centered on the crystallographic results. We did not have ChemDraw or many of today’s computer tools I view with envy. Much of my work was done on a CDC6400 mainframe using custom software developed by Dr. Rossmann’s team and others in the crystallography community. Graphics, some meant to be used with 3D glasses, were produced on a vector plotter and were sometimes 2-3 feet in length. Structural diagrams and many figures were done in collaboration with a skilled draftswoman, Connie Braun, and prepared for print by our photographer William Boyle. Producing even more complex graphics in today’s world seems to be both easier and harder. The ability to do the graphics is easier but is offset by their increasing complexity. In a way I’m glad I moved into the world of Clinical Chemistry and Healthcare Policy for much of my career.
SAURABH VISHWAKARMA (Sat Mar 28 05:31:24 EDT 2015)
In a way I’m glad I moved into the world of Clinical Chemistry and Healthcare Policy for much of my career.
nare (Wed Mar 22 18:38:23 EDT 2017)
would you provide trial version please?
yiyiwin (Thu Mar 23 02:58:56 EDT 2017)
It's very useful for our chemists.
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