APO
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Literature for insight?
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.
"Damn it George! I told you not to drop me!"
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Corrosive Joeseph
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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
Being well adjusted to a sick society is no measure of one's mental health
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Dr.Bob
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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.
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DDTea
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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...
"In the end the proud scientist or philosopher who cannot be bothered to make his thought accessible has no choice but to retire to the heights in
which dwell the Great Misunderstood and the Great Ignored, there to rail in Olympic superiority at the folly of mankind." - Reginald Kapp.
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zed
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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]
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JJay
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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]
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Dr.Bob
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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&...
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DDTea
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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.
"In the end the proud scientist or philosopher who cannot be bothered to make his thought accessible has no choice but to retire to the heights in
which dwell the Great Misunderstood and the Great Ignored, there to rail in Olympic superiority at the folly of mankind." - Reginald Kapp.
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AvBaeyer
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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 700 times
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JJay
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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]
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AvBaeyer
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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
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Dr.Bob
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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.
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JJay
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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.
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BromicAcid
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| 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.
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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]
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ELRIC
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Hey Bromic,
When you mentioned Electron Flow in Organic Chemistry, where you referring to the
book written by Paul Scudder?
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CharlieA
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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"!
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Texium
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Thread Moved
2-1-2017 at 23:01 |
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