Sciencemadness Discussion Board

Literature for insight?

APO - 26-12-2016 at 03:56

Hello all, I haven't posted in the actual science section for a good while since I haven't been able to practice any chemistry; won't be able to for a decent while either. So, for now I'm left with being an armchair academic.

For the more experienced in the forum, what books have helped you gain any chemical insight? Not just for amateur procedures, but for designing synthetic processes or theorizing reactions as well.

Mention of powerful theories or methodology to research is appreciated also; i.e. retrosynthetic analysis seems like an interesting approach for tackling difficult to synthesize organic compounds.

Corrosive Joeseph - 26-12-2016 at 10:34

For planning routes to target compounds.......................

http://www.sciencemadness.org/library/books/Weygand_and_Hilg...

This is one of my favourite chemistry books ever. I would rate it highly...........................

/CJ

Dr.Bob - 26-12-2016 at 11:34

What level are you looking for, beginning, medium, or already have a BS in chemistry?

I have quite a few good books on chemistry at several levels, just need to know a more focused area to narrow it down. Mostly organic? There are quite a few older ones that are good at a beginning level. Fieser's lab book, several books on organic chemistry in general, and then lots of more complex ones.

DDTea - 26-12-2016 at 16:03

Robert Grossman - The Art of Writing Reasonable Organic Reaction Mechanisms

has been, by far, the most useful book to me for teaching me how to think about organic transformations. Work all the problems. Struggle with them. It's worth it.

Also, Anslyn & Dougherty's Modern Physical Organic Chemistry is the grown up version of O. Chem. Hmm. Ian Fleming's book on molecular orbitals is good too. Laszlo Kurti's "Strategic Application of Named Reactions" is a fantastic, readable reference of some of the most useful synthetic reactions. Still waiting for a second edition...

zed - 28-12-2016 at 16:48

Me, I like the Merck index. Older copies are fine. It's a good basic starting point.

Spent a large portion of my life, having one within arm's reach.

Thousands and thousands of chemicals, their structures, and references to their synthesis, right at your finger tips. Some of the older editions, have a named reaction index.

Like books on PharmChem. http://www.pharmpress.com/files/docs/EssentialsPharmaceuticalChemistry_Sample(2).pdf

If you're working on a long complicated synthesis, often the desired end-product, is headed to the medicine cabinet.



[Edited on 29-12-2016 by zed]

JJay - 28-12-2016 at 17:33

I would probably rank myself as intermediate. I had a chemistry minor in college. I know a lot of chemists, and there is a chemistry postdoc and a pharmacy master's in the family, but there is a lot I don't know. I am looking for books on how to determine organic reaction conditions.

I also like books on analytical chemistry since I don't have any fancy GC/MS equipment.

I'd like to do some reading about inorganic p-chem.

I remember reading the Golden Book of Chemistry Experiments in elementary school after finding it in the library. It's a good book. There was a similar book that I owned as a child that I can't remember the name of... it covered a broader range of topics but had cool experiments like adding detergent to hydrochloric acid and putting zinc in it to create explosive soap bubbles.



[Edited on 29-12-2016 by JJay]

Dr.Bob - 28-12-2016 at 19:21

If anyone is looking for anything specific, I posted a list of some almost free books a while back and only got a few requests, but I will confess that I was slow to get back even on those. I am clearing out my storage space, so the next few months will be a good chance for me to find some of these, plus I have many more now available not on the list below.

The list below is only about half of the list. So if people have lists of topics, I can try to find some books for them, all you pay is the media mail postage cost, about $5-10 for a few to a box full of books. I do have a few old copies of the Merck Index, as well as many older general chemistry and organic chemistry texts. It will take me a while to find whatever you might want, and books are subject to prior sale. But if you are interested in some cheap books, it is one way to get a lot of them. If you will be in NC, I can even give them to you free. I have the largest number of books on toxicology, environment, worker safety, cancer and all related topics, but also many on drug discovery, analytical chem, genetics, biochem, nucleic acids and their chemistry, and much more. The list only has about half of them, I just don't have a perfect list, but it is representative of the types.

http://www.sciencemadness.org/talk/viewthread.php?tid=64972&...

DDTea - 28-12-2016 at 19:36

Quote: Originally posted by JJay  
I am looking for books on how to determine organic reaction conditions.


Do it the way organic chemists do: reaction screens/trial and error! Vary catalyst loadings, temperature, time, etc. Get comfortable monitoring reactions/kinetics by appropriate analytical techniques. It's a massive amount of work to be sure.

With enough booky knowledge, you can have an idea of what to look out for--side reactions and such. If there are no expected side reactions, then let it run overnight. Or over 3 nights. A reaction that goes to completion is easier to work up. But ultimately, so much o. chem. is empirical. Did the reaction go? If not, heat it up. Did it exotherm into oblivion? Try combining reagents at reduced temperature, then warming it up. The only way to do this is to experiment on microscale, then scale up for your money shot. The less finicky your reaction is to conditions, the better luck you'll have for a multi-step synthesis.

Of course, a lot of people don't have the patience for this sort of repetitive failure. As a physical organic guy, I subscribe to the philosopy of "no wasted data." Every experiment teaches you something...with the caveat that it's reproducible.

AvBaeyer - 31-12-2016 at 14:07

JJay

With regard to your request about a book for determining how to determine reaction conditions, here is one which may give you some insight. It is one volume in an excellent series short undergrad level texts. Other volumes are noted in the one I have attached. At the end of the day, though, you must experiment!

AvB

Attachment: Research_Techniques_in_Organic_Chemistry.pdf (1.9MB)
This file has been downloaded 786 times

JJay - 31-12-2016 at 14:28

AvBaeyer: I appreciate it, but this book doesn't say anything about how to determine reaction conditions. I've read several similar books, and I'm actually pretty familiar with how to use organic lab equipment.

What I'm looking for is a book describing the methodology for taking a named reaction out of an organic textbook or reference and applying it to specific compounds. The only ways that I'm are aware of are through extensive experimentation or attempting to adapt reaction conditions previously found to work for similar substances.


[Edited on 31-12-2016 by JJay]

AvBaeyer - 31-12-2016 at 14:43

JJay,

I should have been more clear - see the references and suggestions in the Preface. Therein are the sorts of references that you need to follow up on to get insight into reaction conditions. In particular, see the "To find precedents for a reaction" section. There is no real text or book that has the magic answers for determining reaction conditions ab initio. Almost every reaction starts with a "reason by analogy" approach then goes through an experimental optimzation process if necessary. The amount of work that one puts into the optimzation depends on individual goals for the particular reaction. At the end of the day, determining reaction conditions at the outset are primarily a matter of experience and knowledge of the literature. The more you do the better you become. Organic chemistry remains an experimental science.

AvB

Dr.Bob - 1-1-2017 at 16:28

I think what you are looking for is called grad school. Much of the thought depends on the goals, for synthetic chemists, often the goals is just to make some, by any means possible; for process chemists, they want to make it cheap, in few steps, and pure, but don't min a lot of work to do that; and for people here, it may mean finding reactions with easy reagents.

Books on "design of experiment" for chemistry are really good if you are serious, I have done that type of work before to set up a process that might be used for many different chemicals, as opposed to some who want to simply optimize chemistry for only one product.

JJay - 1-1-2017 at 17:31

Quote: Originally posted by Dr.Bob  
I think what you are looking for is called grad school. Much of the thought depends on the goals, for synthetic chemists, often the goals is just to make some, by any means possible; for process chemists, they want to make it cheap, in few steps, and pure, but don't min a lot of work to do that; and for people here, it may mean finding reactions with easy reagents.


That sounds about right. Really, I have all of those goals. Usually, what I'm most interested in is how to make "some." But reactions that take a long time can take months or even years to properly optimize if you don't have a huge lab with a large array of equipment. Sometimes, experiments can't really be performed on a microscale level either.
Quote:


Books on "design of experiment" for chemistry are really good if you are serious, I have done that type of work before to set up a process that might be used for many different chemicals, as opposed to some who want to simply optimize chemistry for only one product.


Design of Experiment is a good topic... it's a little more advanced than what I'm looking for, but I have a rather extensive background in statistics and optimization, so I understand that sort of thing. If you are working with a lot of variables, you can often find the best reaction conditions by hill climbing or something like simulated annealing, but usually I'm more concerned with simply knowing things like whether it is better to perform a reaction in an ice bath, at room temperature or at reflux, in dilute conditions, saturated conditions or what, whether a catalyst is necessary, etc.

I'd like to shortcut the experimental process as much as possible, especially in finding initial reaction conditions that produce at least some amount of the desired product.

BromicAcid - 1-1-2017 at 18:41

Quote: Originally posted by DDTea  
Robert Grossman - The Art of Writing Reasonable Organic Reaction Mechanisms

has been, by far, the most useful book to me for teaching me how to think about organic transformations. Work all the problems. Struggle with them. It's worth it.


I second this, an approachable text with a beautiful systematic approach. I picked it up five or so years out of college and it brought me up to speed again quickly (albeit with a little frustration). I also recommend Electron Flow in Organic Chemistry.

[Edited on 1/2/2017 by BromicAcid]

ELRIC - 2-1-2017 at 14:23

Hey Bromic,

When you mentioned Electron Flow in Organic Chemistry, where you referring to the
book written by Paul Scudder?

CharlieA - 2-1-2017 at 18:17

I'm not referring to any specific source (because I can't remember), but the best advice I ever read/heard for understanding chemistry was to "follow the electrons"!