Interest in "Molecular Design Golf"?

Question

I didn't have much time to participate this fall, and I'm excited to see the synthesis golf questions.

Idea:

I'd like to suggest possibilities for “molecular design golf” (name TBD). These are questions that point to the diversity and design aspects of chemistry. Some might include or require computational investigations, but I’d hope that’s not always required for participation.

The key is to propose a question that must be solved with a molecular structure design.

The catch is to ensure the question isn't too broad (e.g., What gas has the highest refractive index?)

So my suggestion is that the question must require some sort of limit, in molecular size or complexity.

Examples:

There have been a few examples that I think would qualify, e.g.:

• Propose a structure for $\ce{C20H18}$ with the longest IUPAC name.
• Is Hexafluorocyclohexane the “Most Polar” Small Molecule? (limited to 30 atoms)

Meta Question: Is it worth pursuing "molecular design golf" separate from "synthesis golf?" If so, please suggest some possible questions, even if they're not completely well-formed.

Answer 1

I figure I'll write something since I am enjoying some precious time away from the bench and can actually afford to do so...

As I mention in my comment, this format has great potential to uncover some fundamental aspects of chemistry. That said, I think the success of this format will be rather heavily dependent on the breadth we're willing to accept. In particular, I would like to make a case for the inclusion of questions regarding extremes in chemistry.

Now, I'll admit a large personal bias right from the outset. I love talking and reading about "what is the most/least ____ possible in chemistry?" because it helps establish the boundaries of our Universe and the limits of our knowledge. It's awesome to see how crazy a system can get because someone just really really wanted it to display as much of a certain behaviour as is physically allowed.

I do not think that the fact that extremes are eventually superseded is a good argument against their inclusion. For one, that's what science is all about. There is never a "right" answer, only better and better approximations to reality. No matter what, a significant fraction of answers currently on the site will be superseded or made obsolete in the next few decades (reaction mechanisms, chemical/physical standards, experimental setups, industrial processes, etc); all knowledge has a half-life.

Even when something is superseded, that in no way means the prior information is now useless, especially if we emphasise the journey rather than the destination. Therefore, instead of giving answers like:

• "this molecule is the highest, see ref here"

, we should gravitate towards something like:

• "as of 2018, this molecule is the highest known. It makes extensive use of properties X, Y and Z. Property X seems to be at its limit, but it may be possible to exploit Y and Z further. An intuitive argument suggests there must be an upper limit, and detailed theoretical analysis confirms that there can be no example which is twice more than the current experimental limit"

Also, from a purely practical standpoint, the allowance of "extreme" questions immediately provides a huge pool of topics to explore, along with the chemistry within them.

I know there's already been some discussion on this and I wasn't around for it, so I apologise if my arguments have been raised and refuted previously. I am happy to take criticism.

Answer 2

This answer ~reproduces my comments from below the OP, and adds a few more.

This idea reminds me a bit of the concept behind Programming Puzzles & Code Golf. My sense is they developed a lot of their most common rules/limitations as they went along, and saw where the fun-killing shortcuts were. Likely the evolution would be similar for this. Worth a shot, I say! I might even be able to play!!

I concur with Marko, the objective functions need to be concrete computable, calculable, or researchable (e.g., in reference databases) chemical quantities; for computational challenges this would entail accepting the inevitable tension that computed values do not always match well with experimental ones. A well-posed computational challenge may well need to specify things like computational method and parameters, possibly the software package to use (presumably free/open-source), and some challenges at least should ideally be constrained to relatively small molecules so that those without significant computational resources can still participate. Database lookup challenges would ideally constrain answers to come from one or more open data sources. Any answers not conforming to the challenge criteria would then be non-competing.

One other thing to consider implementing as a part of this would be something like the Sandbox for Proposed Challenges implemented at PPCG, where draft challenges are posted for comment by interested members of the community. These sorts of discussions could start here, but there'd be value at least in creating a separate meta post for it, so that discussions on the overarching idea itself would be held separately from the individual discussions on challenge ideas. (Something similar to this is developing with Synthesis Golf, with an overview post living separately from the 'synthesis golf target ideas' post.

Answer 3

I like the idea, and have just bountied the first instalment.

However, I just want to write some of my thoughts. It may or may not be useful, but it is just my 2p.

One has to be clear about the aims of such an initiative. I think that it is certainly fun for people who know how to look for answers. Could it, perhaps, attract new people who may stay and become regular users...? I'm reminded, of course, of synthesis-golf which started about half a year ago. Despite objections that it would be too broad I remain a strong supporter of it, because I generally want to raise the quality of Q&A and I think that that would be able to contribute to that larger aim. My view on molecular-design is similar.

However, as with synthesis-golf, I worry that the people who can answer this are few to begin with. syngolf started out fairly strong, but two of the last three challenges have only had one answer. That could be due to my admittedly poor choice of molecule, but also I think that some people who have taken part previously find themselves quite busy. Personally, I do not have either the time or energy to participate fully, especially when my "spare time" on SE consists of moderation work (not actually all that much) and editing work (literally endless). So now the number of people who (1) know how to answer; and (2) are free enough to answer is low. I also perceive a general lack of interest on its meta posts, which is probably because of the same reasons.

So, if this is (partly) about raising quality of Q&A, I wonder if we are doing it the correct way round. Is the time ripe for this kind of initiative - is the userbase sufficiently large? Or is there another way that the quality should be addressed? Obviously, if it is fun, then by all means - there's no harm, apart from the opportunity cost of time.

I remain in support of the idea; this is really just me sharing some insecurities I have, towards syngolf and similar projects. I would be very happy to see the inaugural molecular-design prove my concerns unfounded.