- You can buy tetra-tert-butylmethane from (at least) the following vendors:
- Angene
- Triveni
- Hangzhou Sage Chemical Co., Ltd
- Kingston Chemicals
- Atomax Chemical Co., Ltd.
- Tetra-tert-butylmethane has never been made and likely cannot be made.
Aside from being a favourite high-school chemistry nomenclature problem, PubChem and ChemSpider both have entries for this compound. It has CAS number: 4103-17-7. And it does not exist.
So, I went searching.
Chemical vendors of tetra-tert-butylmethane (TTBM)
Angene
Triveni
At least they have the decency to use the word "would"--in the event it does exist, it would be the most compact isomer of heptadecane.
Hangzhou
Sage could not find the compound I was looking for. It does say I can contact their chemists directly. That sounds like a good idea.
Kingston Chemicals
Does the TTBM glow light blue in the test tube?
Atomax
I cannot find it on Atomax, even though it is listed as a supplier.
Why is a chemical like this even in databases?
MolBase actually quotes the reference price of this compound at $308/g. Not bad. How long do I need to wait before you send me the bottle?
Current research on tetra-tert-butylmethane (TTBM)
Google Scholar picks up only about 20 articles from the search term "tetra-tert-butylmethane". All of them suggest that TTBM has not yet been synthesized.
Since I cannot access the 1978 article from BULLETIN DES SOCIÉTÉS CHIMIQUES BELGES (Wiley Online Library), let's begin in 1981, where a fascinating article entitled "How many rings can share a quaternary atom?" studies ring structures made from TTBM, but does not discuss TTBM. It does however claim that the following compound tetra-tert-butyltetrahedrane ( SMILES: C13(C(C)(C)C)C2(C(C)(C)C)C3(C(C)(C)C)C12(C(C)(C)C) )
was actually synthesized and confirmed by 13C NMR.
Again, I don't have access to the theoretical study in 1985 about permethylcyclopentane. The study in 1990 only mentions TTBM as an interesting example of molecular fractal notation.
The smallest alkane that cannot be made was decided to be TTBM based on studies of calculated bond lengths. A later study, also by Goodman, confirmed the structure of TTBM less one peripheral methyl group is also too unstable. The calculations of bond lengths in these molecules give results of up to 5 Angstroms, strongly suggesting that the bond is in fact homolytically cleaved and breaks into radicals.
So, even though TTBM passes the "diagnostic" test of fitting into a diamond lattice, it likely cannot be synthesized.
AND the smallest alkane that cannot be made is not TTBM, but is the same molecule less one methyl group--isopropyl-tri-tert-butylmethane (ITTBM).
Summary
There are still (0) items in my cart.
References
So, I went searching.
Chemical vendors of tetra-tert-butylmethane (TTBM)
Angene
Triveni
At least they have the decency to use the word "would"--in the event it does exist, it would be the most compact isomer of heptadecane.
Hangzhou
Sage could not find the compound I was looking for. It does say I can contact their chemists directly. That sounds like a good idea.
Kingston Chemicals
Does the TTBM glow light blue in the test tube?
Atomax
I cannot find it on Atomax, even though it is listed as a supplier.
Why is a chemical like this even in databases?
MolBase actually quotes the reference price of this compound at $308/g. Not bad. How long do I need to wait before you send me the bottle?
Current research on tetra-tert-butylmethane (TTBM)
Google Scholar picks up only about 20 articles from the search term "tetra-tert-butylmethane". All of them suggest that TTBM has not yet been synthesized.
Since I cannot access the 1978 article from BULLETIN DES SOCIÉTÉS CHIMIQUES BELGES (Wiley Online Library), let's begin in 1981, where a fascinating article entitled "How many rings can share a quaternary atom?" studies ring structures made from TTBM, but does not discuss TTBM. It does however claim that the following compound tetra-tert-butyltetrahedrane ( SMILES: C13(C(C)(C)C)C2(C(C)(C)C)C3(C(C)(C)C)C12(C(C)(C)C) )
Again, I don't have access to the theoretical study in 1985 about permethylcyclopentane. The study in 1990 only mentions TTBM as an interesting example of molecular fractal notation.
The smallest alkane that cannot be made was decided to be TTBM based on studies of calculated bond lengths. A later study, also by Goodman, confirmed the structure of TTBM less one peripheral methyl group is also too unstable. The calculations of bond lengths in these molecules give results of up to 5 Angstroms, strongly suggesting that the bond is in fact homolytically cleaved and breaks into radicals.
So, even though TTBM passes the "diagnostic" test of fitting into a diamond lattice, it likely cannot be synthesized.
AND the smallest alkane that cannot be made is not TTBM, but is the same molecule less one methyl group--isopropyl-tri-tert-butylmethane (ITTBM).
Summary
There are still (0) items in my cart.
References
- Angene Product Details: Pentane, 3,3-bis(1,1-dimethylethyl)-2,2,4,4-tetramethyl-, http://www.angenechemical.com/productshow/AGN-PC-000GS9.html.
- Triveni Search by Letter, T, http://trivenichemicals.go4worldbusiness.com/products.aspx?searchby=t, India.
- Huangzhou Sage Chemicals Co., Ltd. search page. http://www.sagechem.com/search.asp
- Kingston Chemicals product page, http://www.kingstonchem.com/productshow/KST-13996992.html
- MolBase reference page, http://www.molbase.com/en/name-%20Tetra-tert-butylmethane.html.
- How many rings can share a quaternary atom? Peter Gund and Tamara M. Gund. Journal of the American Chemical Society 1981 103 (15), 4458-4465. http://dx.doi.org/10.1021/ja00405a028
- Maier, G., Pfriem, S., Schäfer, U. and Matusch, R. (1978), Tetra-tert-butyltetrahedrane. Angew. Chem. Int. Ed. Engl., 17: 520–521. http://dx.doi.org/10.1002/anie.197805201
- Synthesis and characterization of the f(1.2) molecular fractal, 5,5-bis(3',3'-dimethylbutyl)-2,2,8,8-tetramethylnonane. G. David Mendenhall, S. X. Liang, and E. H. T. Chen. The Journal of Organic Chemistry 1990 55 (11), 3697-3699. http://dx.doi.org/10.1021/jo00298a068
- What Is the Smallest Saturated Acyclic Alkane that Cannot Be Made? K. M. Nalin de Silva† and and Jonathan M. Goodman*. Journal of Chemical Information and Modeling 2005 45 (1), 81-87. http://dx.doi.org/10.1021/ci0497657
- Exploration of the Accessible Chemical Space of Acyclic Alkanes. Robert S. Paton and and Jonathan M. Goodman*. Journal of Chemical Information and Modeling 2007 47 (6), 2124-2132. http://dx.doi.org/10.1021/ci700246b
No comments:
Post a Comment