Chemical Forums

Please login or register.

Login with username, password and session length

Sponsored links

Pages: [1]   Go Down

Author Topic: Curved line  (Read 722 times)

0 Members and 1 Guest are viewing this topic.

Raderford

  • Sr. Member
  • *****
  • Mole Snacks: +34/-22
  • Offline Offline
  • Gender: Male
  • Posts: 1259
Curved line
« on: September 19, 2012, 06:29:31 AM »

http://en.wikipedia.org/wiki/Glyceraldehyde on the picture right, there is an OH group attached to a C atom with a curved line. I saw a table below where that line is changed with a dashed or with a bold line (which represent the space arrangement of the OH group in the two enantiomers).
Does the curved line then represent the OH group space arrangement of the racemic mixture?
Logged
Need help with deriving mechanisms from rate laws.

discodermolide

  • Chemist
  • Sr. Member
  • *
  • Mole Snacks: +256/-62
  • Online Online
  • Gender: Male
  • Posts: 3416
Re: Curved line
« Reply #1 on: September 19, 2012, 06:31:15 AM »

It's a wavy live and depicts unknown stereochemistry.
Logged
Development Chemists do it on Scale, Research Chemists just do it!

Raderford

  • Sr. Member
  • *****
  • Mole Snacks: +34/-22
  • Offline Offline
  • Gender: Male
  • Posts: 1259
Re: Curved line
« Reply #2 on: September 19, 2012, 06:37:02 AM »

Unknown because the configuration of the molecule wasn't given, right?
Logged
Need help with deriving mechanisms from rate laws.

discodermolide

  • Chemist
  • Sr. Member
  • *
  • Mole Snacks: +256/-62
  • Online Online
  • Gender: Male
  • Posts: 3416
Re: Curved line
« Reply #3 on: September 19, 2012, 06:43:46 AM »

Unknown because the stereochemistry of the C atom is not known.
Logged
Development Chemists do it on Scale, Research Chemists just do it!

Babcock_Hall

  • Chemist
  • Full Member
  • *
  • Mole Snacks: +62/-4
  • Offline Offline
  • Posts: 803
Re: Curved line
« Reply #4 on: September 19, 2012, 07:06:43 AM »

At the risk of splitting hairs, I would say that the stereochemistry is deliberately not specified when one uses a wavy bond.  Both D-glyceraldehyde and L-glyceraldehyde are well-characterized compounds.  I hope this helps, rather than confuses.
Logged

Raderford

  • Sr. Member
  • *****
  • Mole Snacks: +34/-22
  • Offline Offline
  • Gender: Male
  • Posts: 1259
Re: Curved line
« Reply #5 on: September 19, 2012, 07:51:44 AM »

Unknown because the stereochemistry of the C atom is not known.
I mean the same, but didn't express well.
At the risk of splitting hairs, I would say that the stereochemistry is deliberately not specified when one uses a wavy bond.  Both D-glyceraldehyde and L-glyceraldehyde are well-characterized compounds.  I hope this helps, rather than confuses.
Understood.
Thanks both.
Logged
Need help with deriving mechanisms from rate laws.

fledarmus

  • Chemist
  • Sr. Member
  • *
  • Mole Snacks: +197/-28
  • Offline Offline
  • Posts: 1679
Re: Curved line
« Reply #6 on: September 19, 2012, 09:26:13 AM »

At the risk of beating a dead horse:

Racemic mixture has a specific meaning - it is a 1:1 mix of two enantiomers. While a racemic mixture may, in some contexts, be represented by a wavy bond, the use of the wavy bond is far more general than that single meaning and gives no information whatsoever (in itself) on the proportions of any possible mixture.

The wavy line bond is used in many different ways, depending on context. In the context shown, it means what Babcock_Hall said - the stereochemistry is not specified. The name "glyceraldehyde" with no other descriptors does not show chirality, and the wavy bond in the structure makes that obvious.

It can also mean "unknown chirality" as Discodermolide said. This is usually in the context of a reaction, and I've seen it most frequently in reactions that add a second chiral center to a chiral molecule. This produces diastereomers, and you frequently see some stereocontrol over the second chiral center by the first chiral center. The products are frequently separable by chromatography, but it can take considerable work to determine what the exact structures of the two resulting compounds are. Frequently, both the mixture of diastereomers and the individual diastereomers are represented with a wavy bond until the actual stereochemistry can be determined.

Finally, it is used in some contexts to indicate "not determined" or "not important". This is the case frequently in natural products which have multiple stereocenters, such as steroids. A reaction may produce a new stereocenter which is removed by a subsequent reaction - for example, a hydrolysis reaction to produce an alcohol on a new chiral center, followed by oxidation to the ketone. Steroids are rigid systems and many reactions are very stereoselective, so the hydrolysis reaction will probably yield mostly a single enantiomer - but if you are getting rid of the stereocenter anyway in the next reaction, it probably isn't worth the effort to prove that and determine the exact stereochemistry. Instead, you just represent the C-OH bond with a wavy line, and go on to the next reaction.

There - dead horse is thoroughly flogged.  :)
Logged

Raderford

  • Sr. Member
  • *****
  • Mole Snacks: +34/-22
  • Offline Offline
  • Gender: Male
  • Posts: 1259
Re: Curved line
« Reply #7 on: September 20, 2012, 02:09:42 AM »

What if Z and E configurations aren't given (for a double bond), how to represent this?
Logged
Need help with deriving mechanisms from rate laws.

discodermolide

  • Chemist
  • Sr. Member
  • *
  • Mole Snacks: +256/-62
  • Online Online
  • Gender: Male
  • Posts: 3416
Re: Curved line
« Reply #8 on: September 20, 2012, 02:13:20 AM »

In the same way.
Logged
Development Chemists do it on Scale, Research Chemists just do it!

fledarmus

  • Chemist
  • Sr. Member
  • *
  • Mole Snacks: +197/-28
  • Offline Offline
  • Posts: 1679
Re: Curved line
« Reply #9 on: September 20, 2012, 02:33:13 AM »

What if Z and E configurations aren't given (for a double bond), how to represent this?

Ooops - yes, I totally forgot that one. Good catch!

Any other uses for a wavy bond?

Logged

Raderford

  • Sr. Member
  • *****
  • Mole Snacks: +34/-22
  • Offline Offline
  • Gender: Male
  • Posts: 1259
Re: Curved line
« Reply #10 on: September 20, 2012, 03:03:44 AM »

In the same way.
Okay, thanks.
What if Z and E configurations aren't given (for a double bond), how to represent this?

Ooops - yes, I totally forgot that one. Good catch!

Any other uses for a wavy bond?
Maybe for cyclic compounds with two substituents (I think that it is Bayer's isomerism) when you don't know if the substituents are above or under the plane of the ring.
Logged
Need help with deriving mechanisms from rate laws.

Arkcon

  • Global Moderator
  • Sr. Member
  • ***
  • Mole Snacks: +284/-105
  • Offline Offline
  • Posts: 3994
Re: Curved line
« Reply #11 on: September 20, 2012, 03:08:54 AM »


Any other uses for a wavy bond?

Sadly, I have one.  Sometimes beginner biology courses draw the bond of the last phosphate group in ATP with a squiggly line, as shorthand for some sort of "high energy bond" for ATP to release its "energy currency" for a living process.  We're going to have to remain alert for that, because the multiple definitions is going to confuse some student at some time.
Logged
That all depends on how reasonable we're all willing to be.  I just want my friends back, except for Cartman, you can keep him.
Pages: [1]   Go Up
 

Mitch Andre Garcia's Chemical Forums 2003-Present.

Page created in 0.081 seconds with 21 queries.