Shared posts

04 Sep 15:33

Dynamic self-correcting nucleophilic aromatic substitution

by Wen Jie Ong

Dynamic self-correcting nucleophilic aromatic substitution

Dynamic self-correcting nucleophilic aromatic substitution, Published online: 03 September 2018; doi:10.1038/s41557-018-0122-8

Dynamic covalent chemistry offers promise for the formation of elaborate extended network materials in high yields, but the limited number of reactions available confines the scope and functionality of the materials synthesized. Now, nucleophilic aromatic substitution has been shown to be reversible, and thus self-correcting, enabling the easy synthesis of sulfur-rich materials.
08 May 21:16

Sequential Synthesis, Olfactory Properties, and Biological Activity of Quinoxaline Derivatives

by Mia Imanishi, Motohiro Sonoda, Hironari Miyazato, Keiichiro Sugimoto, Mitsugu Akagawa and Shinji Tanimori

TOC Graphic

ACS Omega
DOI: 10.1021/acsomega.7b00124
15 Feb 14:21

Ice Nucleation Efficiency of Hydroxylated Organic Surfaces Is Controlled by Their Structural Fluctuations and Mismatch to Ice

by Yuqing Qiu, Nathan Odendahl, Arpa Hudait, Ryan Mason, Allan K. Bertram, Francesco Paesani, Paul J. DeMott and Valeria Molinero

TOC Graphic

Journal of the American Chemical Society
DOI: 10.1021/jacs.6b12210
22 Oct 17:38

Intermolecular Reactions of a Foiled Carbene with Carbonyl Compounds: The Effects of Trishomocyclopropyl Stabilization

by Ingrid Malene Apeland, Murray G. Rosenberg, Vladimir B. Arion, Hanspeter Kählig and Udo H. Brinker

TOC Graphic

The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.5b01988
23 Sep 12:32

Comic for 2015.09.23

New Cyanide and Happiness Comic
01 Sep 02:25

Mini Black Bean Turkey Burgers

by Beth M

One of my favorite techniques for stretching my food budget is substituting half of the meat in my meals with beans. So, when I got an email from one of my readers, Lori, with a link to this Black Bean Turkey Burger recipe on Allrecipes.com, I had to go check it out. It looked super simple and tasty, but I wanted to make my own version. I took a cue from Lori, who said she liked to add her own spices, like cumin and sriracha, and decided to throw a southwest spin on the black bean and turkey combo.

I used a simple mix of chili powder, cumin, garlic, and cayenne to flavor the beans and meat, then added sliced green onion for some color, texture, and flavor. That’s it! That’s all you need to make an insanely delicious black bean turkey burger. You can eat these patties on a bun, but I opted for pita bread because they tend to be less expensive where I live. I added a few slices of tomato and made a simple avocado-sour cream sauce because avocado were on sale. The sauce was just for fun, really, so you can skip it if needed, or even just do sliced avocado if you’re short on time.

Why did I make them “mini”? Because A) they cook faster and B) two small patties will fit in my pita better than one large patty. So, feel free to make regular sized patties if you want, just know that they’ll like need to cook a little longer.

AND, if you want to be extra fancy, you can mix some shredded pepper jack into the meat and bean mixture for little pops of cheesy goodness in your burgers. HELLO YUM.

Mini Black Bean Turkey Burgers - BudgetBytes.com

4.7 from 9 reviews
Mini Black Bean Turkey Burgers
 
Prep time
Cook time
Total time
 
Total Cost: $9.81
Cost Per Serving: $1.96
Serves: 5 (two patties each)
Ingredients
BURGERS
  • 1 15oz. can black beans* $0.60
  • 3 green onions $0.38
  • ½ Tbsp chili powder** $0.15
  • ½ tsp cumin $0.05
  • ½ tsp garlic powder $0.02
  • ⅛ tsp cayenne pepper $0.03
  • ½ tsp salt $0.04
  • 19oz. package lean ground turkey $4.59
AVOCADO SAUCE (optional)
  • 1 ripe avocado $1.00
  • ½ lime $0.20
  • ⅛ tsp garlic powder $0.02
  • ½ tsp salt $0.02
  • ½ cup sour cream $0.75
  • ½ tsp sugar $0.01
BURGER TOPPINGS
  • 5 pita halves $0.83
  • 2 Roma tomatoes, sliced $1.12
Instructions
  1. Preheat the oven to 375 degrees. Drain and rinse the black beans. Place the black beans in a large bowl and mash them slightly with your hands or a potato masher. Slice the green onions and add them to the bowl along with the chili powder, cumin, garlic powder, cayenne pepper, and salt. Stir until the beans are evenly seasoned.
  2. Add the ground turkey to the seasoned black beans. Mix well using your hands. Form 10 small patties (about 2-2.5 inches diameter, ½ inch thick). Place the patties on a roasting pan or a baking sheet covered with foil and wire cooling racks.
  3. Bake the patties in the preheated oven for 20 minutes, or until browned on the outside and no longer pink in the center. Alternatively, you can cook the patties in a skillet, on a grill, or using an indoor countertop grill.
  4. While the patties are baking, prepare the avocado sauce. Add the avocado (diced), juice from half a lime (about 2 Tbsp), garlic powder, salt, sugar, sour cream, and 2-4 Tbsp of water to a blender. Blend the ingredients together, adding the water slowly until a smooth, thick sauce forms.
  5. Smear some of the sauce inside each pita half, add a couple tomato slices, and two of the turkey patties.
Notes
*I used black beans that I had cooked from dry in my slow cooker.

**Chili powder is a mild blend of spices, not hot red pepper powder.
3.3.3070

Mini Black Bean Turkey Burgers - BudgetBytes.com

 

Step by Step Photos

Mashed Black BeansPreheat the oven to 375 degrees. Rinse and drain one 15oz. can of black beans. Place them in a large bowl and use your hands or a potato masher to slightly mash the beans.

Green Onions and SpicesTo the mashed beans add: 3 sliced green onions, 1/2 Tbsp chili powder, 1/2 tsp cumin, 1/4 tsp garlic powder, 1/8 tsp cayenne pepper, and 1/2 tsp salt.

Seasoned Black BeansMix the ingredients the bowl until the beans are well seasoned. If you’re using low sodium canned beans, or beans you’ve cooked yourself without salt, you may want an extra 1/4 tsp salt. If you taste this mixture now, it may be very strong or salty, but remember these seasoning have to spread throughout the turkey as well and will end up much more mild.

Ground TurkeyI’m not sure why ground turkey always comes in 19oz. packages, but they do (here in the U.S. anyway). If your packages aren’t 19oz, you can just use about 1.5 lbs.

Ground Turkey and Black Beans

Add the ground turkey to the bowl and mix with your hands until everything is evenly distributed.

Turkey Burger PattiesForm the mixture into about 10 small patties, 2.5 inches in diameter and about 1/2 inch thick. There are several ways you can cook these patties, including a skillet, a grill, or something like a George Foreman Grill. I chose to bake them because Lori said she likes this method best and because they can just cook all at one time without much babysitting. I made a make-shift roasting pan by covering a baking sheet with foil (for easy cleanup) and placing two wire racks on top. This allows the hot air to circulate under the burgers and for the fat to drip away.

Baked Black Bean Turkey BurgersBake for 20 minutes in the preheated oven. After baking they should be browned and no longer pink in the center. You may need to sacrifice one patty and cut it in half to be sure. Remember, if you make a different sized patty, the baking time will vary.

Avocado Sauce BlendedWhile the patties are baking, you can make the avocado sauce. Add 1 diced avocado, the juice from half a lime (about 2 Tbsp), 1/8 tsp garlic powder, 1/2 tsp salt, 1/2 tsp sugar, and 1/2 cup sour cream to a blender. Blend the ingredients together, adding water slowly (about 4 Tbsp), until you have a thick, smooth sauce.

Mini Black Bean Turkey Burgers - BudgetBytes.comTo make the “burgers”, spread some of the avocado sauce inside half a pita, add a few slices of tomato, and two of the mini black bean turkey burgers.

Mini Black Bean Turkey Burgers - BudgetBytes.comEasy, delicious, and super healthy! Seriously, these burgers come together in just a few minutes and bake quickly, so this is a great weeknight meal option. :D

Mini Black Bean Turkey Burgers - Budgetbytes.com

The post Mini Black Bean Turkey Burgers appeared first on Budget Bytes.

01 Sep 02:22

Creamy Spinach Artichoke Pizza

by Beth M

I’m starting a difficult challenge tomorrow where, like last year’s SNAP challenge, I’m going to attempt to eat only $4.50 worth of food per day. I remember how hungry I was last year, so I kinda wanted to have one last indulgent hurrah just before I started the challenge. What’s the best indulgent food, IMHO? Pizza, of course.

But this isn’t just any pizza. This is a thick crust, crispy edged, pan pizza topped with a rich and creamy spinach sauce, chopped up artichoke hearts, and a final layer of melted mozzarella cheese. Ohhhhh yeeeahhhh.

I decided to make this pizza with the no-knead pan crust, which needs to be started the night before, but you could always do this on a regular pizza crust, or even a super fast thin crust. It’s up to you. I used a 10-inch lodge skillet, but these toppings are enough for a 12-inch pan pizza, or even a 14-inch regular crust pizza. It’s pretty flexible, so you can use your favorite type of crust. I think the thick, fluffy pan crust is perfect with this creamy sauce, though. MMmm.

Creamy Spinach Artichoke Pizza - BudgetBytes.com

5.0 from 7 reviews
Creamy Spinach Artichoke Pizza
 
Prep time
Cook time
Total time
 
Total Cost: $5.14
Cost Per Serving: $1.71
Serves: 3 (2 slices each)
Ingredients
DOUGH
  • 2 cups all-purpose flour $0.30
  • 1 tsp salt $0.05
  • ⅛ tsp instant or bread machine yeast $0.02
  • 1 Tbsp olive oil $0.16
  • ¾ to 1 cup water $0.00
CREAMY SPINACH SAUCE
  • ½ lb. frozen chopped spinach $0.85
  • 1 Tbsp butter $0.10
  • 1 clove garlic $0.08
  • 4 oz. cream cheese $1.00
  • ½ cup milk $0.19
  • ¼ tsp salt $0.02
PIZZA
  • 1 Tbsp vegetable oil $0.02
  • ½ 15oz. can artichoke hearts $1.30
  • Pinch red pepper flakes (optional) $0.05
  • 1 cup shredded mozzarella $1.00
Instructions
  1. Begin the dough the night before. In a large bowl stir together the flour, salt, and yeast. Combine the olive oil and ¾ cup water, then pour it into the bowl with the flour. Stir until a single (slightly wet and sticky) ball of dough forms with no dry flour left on the bottom of the bowl. Add one to two tablespoons more of water, if needed, to form a ball of dough. Loosely cover the dough and let it sit at room temperature for 12-18 hours.
  2. The next day let the spinach thaw and then squeeze out as much moisture as possible. Preheat the oven to 450 degrees and pour 1 Tbsp of vegetable oil into a 10 or 12-inch cast iron skillet. Spread the oil around the skillet, including up the side walls.
  3. To make the sauce, mince the garlic and add it to a small pot along with the butter. Sauté the butter and garlic for 1-2 minutes over medium-low heat, or until the garlic is soft and fragrant. Add the cream cheese, milk, and salt to the butter and garlic. Whisk and cook over medium-low heat until the cream cheese has melted into the milk and a thick sauce forms (3-5 minutes). Finally, stir the squeeze-dried spinach into the sauce, breaking up any clumps as you stir. Remove the sauce from the heat and set aside.
  4. Use the excess oil from the skillet to coat your hands, then scrape the fermented dough out of the bowl. Gently press and stretch the loose dough into the skillet until it evenly covers the bottom.
  5. Spread the creamy spinach sauce over the dough, covering from edge to edge. Drain the artichoke hearts, give them a rough chop, then sprinkle over the creamy spinach sauce. Add a pinch of red pepper flakes, if desired. Finally, top the pizza with the shredded mozzarella.
  6. Bake the pizza in the fully preheated oven for 20-25 minutes, or until the edges are sizzling and the top is golden brown. Remove the pizza from the oven and slide a butter knife around the edges to loosen any melted cheese. Either slide the whole pizza onto a cutting board or carefully slice the pizza in the pan. Cut into six slices and serve.
3.3.3070

Creamy Spinach Artichoke Pizza - BudgetBytes.com

 

Step by Step Photos

Dough StarterIf you’re using the pan pizza dough that I used above, begin the night before. In a large bowl (or pot) stir together 2 cups flour, 1 tsp salt, and 1/8 tsp instant or “bread machine” yeast. Combine 1 Tbsp olive oil and 3/4 cup water, then pour it into the bowl with the flour. Stir until a sticky ball of dough forms with no dry flour left on the bottom of the bowl. If needed, add one to two more tablespoons of water to help it come together in one single piece of dough.

Fermented DoughLoosely cover the dough (that’s why I like using a pot, I just set the lid on slightly crooked) and let it sit at room temperature for 12-18 hours. As it ferments it will spread out and get very bubbly. It will still be quite sticky compared to most bread doughs.

Frozen SpinachOn the day you’re making the pizza, take 1/2 lb. of frozen spinach out of the freezer to thaw (thaw at room temp, or in the microwave for a faster thaw).

Squeeze Dried SpinachOnce the spinach is thawed, squeeze as much moisture out as possible. I just grab a handful and squeeeeze until no more liquid comes out.

Melt Butter and Garlic

Next it’s time to make the sauce (and begin preheating the oven to 450 degrees). Mince one clove of garlic. Add it to a small pot along with 1 Tbsp of butter. Sauté the garlic in the butter over medium-low heat until the garlic is soft and fragrant (about 1-2 minutes).

Add Milk Cream Cheese and SaltAdd 1/2 cup milk, 4 oz. cream cheese, and 1/4 tsp salt to the butter and garlic. Continue to cook over medium-low heat, while whisking, until the cream cheese has melted in and a thick sauce has formed.

Spinach Cream SauceAdd the squeeze dried spinach to the cream sauce and stir until it’s combined (break up any clumps of spinach as you stir). Remove the sauce from the heat and set it aside.

Stretched DoughSpread 1 Tbsp vegetable oil in a 10 or 12-inch cast iron skillet (including up the sides). Use the excess oil in the skillet to coat your hands, then scrape the dough out of its bowl. Carefully stretch and press the dough into the skillet until it evenly covers the bottom.

Spinach Cream Sauce on DoughSpread the spinach cream sauce over the dough from edge to edge.

Chopped Artichoke HeartsDrain one 15oz. can of artichoke hearts. Take half of the can and give them a rough chop (the other half can be frozen or used for a second pizza).

Artichoke Hearts Red Pepper

Sprinkle the chopped artichoke hearts over the pizza. If you like things a little spicy like me, sprinkle on a few red pepper flakes.

MozzarellaFinally, top with one cup of shredded mozzarella.

Baked Creamy Spinach Artichoke PizzaBake the pizza for 20-25 minutes, or until the edges are sizzling and the top is golden brown. Use a butter knife to loosen around the edges where cheese may have melted onto the skillet. Slide the pizza onto a cutting board or carefully slice it while in the pan.

Creamy Spinach Artichoke Pizza - BudgetBytes.comCut into six pieces and serve! This is pretty rich and filling, so two pieces goes a lot further than you think. ;)

The post Creamy Spinach Artichoke Pizza appeared first on Budget Bytes.

29 Aug 18:18

Nutella Brownies

by Tessa

Nutella Brownies are perfectly thick, chewy, fudgy, and slightly gooey with a hint of chocolate hazelnut goodness. One of the best brownies I’ve ever had!
Nutella Brownies are perfectly thick, chewy, fudgy, and slightly gooey with a hint of chocolate hazelnut goodness. One of the best brownies I've ever had!

Running this blog as a full time business can often paradoxically mean a lot of time away from the kitchen. There’s a lot of behind-the-scenes work that goes into everything. That sometimes means getting relaxed time in the kitchen is like a special treat. Until I make a giant mess and am staring down a huge stack of dirty dishes. But luckily when a recipe turns out the dishes are a small price to pay for a taste of something delectable. There’s a special gratification that comes from a homemade kitchen success and it feels that much better when it’s a recipe you’ve written and created.

Nutella Brownies are perfectly thick, chewy, fudgy, and slightly gooey with a hint of chocolate hazelnut goodness. One of the best brownies I've ever had!

Now, Nutella Brownies aren’t all that original. But this recipe is based off my Ultimate Brownie recipe which took SIX+ batches to perfect. I tweaked that recipe slightly by adding a bunch of Nutella, of course, and some other tweaks like a bit of cocoa powder to absorb some of the extra moisture. The result is something magnificent. I hope the photos really capture just how rich, fudgy, and gooey these brownies are. Nutella brownies + cold glass of milk = my idea of perfect. What’s yours?

CLICK HERE TO GET THE FULL RECIPE & MORE!Nutella Brownies

The post Nutella Brownies appeared first on Handle the Heat.

19 Aug 14:21

Baran Invents Time Machine, Returns To 2015 To Report On Maoecrystal V

by C&EN Onion
Boston, MA

To an audience of eager chemists, Professor Phil Baran of the Scripps Institute presented his future self from the year 2019 who in turn presented the results of his present self's eventual optimized total synthesis of maoecrystal v.  Baran, who will have had completed the elegant, 12-step route by late 2018, extolled on the difficulties of the project.

"Optimizing and cutting down on junk steps took almost two full years of work by seven post-docs.  From there, it was a trivial matter of correctly orienting the polarity of several flux capacitors, allowing me to be here with you today," said future-Baran.

Baran did, however, acknowledge some difficulties in implementing his time travel machine.  "It turned out the baryon transistors were exceedingly sensitive to tachyon magnetization.  The result was inconsistent end-points of time travel.  I regret to report that, in the course of debugging, two graduate students were lost, we believe sometime in the mid-to-late cretaceous period."

Upon completion of his talk, the future-present Baran system auto-annihilated, resulting in a singular meta-Baran, which itself transcended both time and mortality, as well as human consciousness.  

All those in attendance were reportedly filled with an overwhelming feeling of tranquility and understanding of the collective human condition. Meta-Baran then disintegrated into pure energy, a sight so beautiful that many were driven insane by the jarring epiphany that nothing in the duration of their metaphysically unimportant lives would ever compare.

As of press time, a small slip in the fabric of space-time had allowed fleeting contact with Professor Yoshito Kishi from the year 2021, who uttered a drawn out "MAIIIITOOOOOTOOOXIIIIIIN" before fading from existence.
06 Aug 18:46

First Total Synthesis of Trehalose-Containing Branched Oligosaccharide OSE-1 of Mycobacterium gordonae (Strain 990)

by Manishkumar A. Chaube, Suvarn S. Kulkarni

Abstract

The first total synthesis of the branched oligosaccharide OSE-1 of Mycobacterium gordonae (strain 990) is reported. An intramolecular aglycon delivery approach was used for constructing the desymmetrized 1,1′-α,α-linked trehalose moiety. A [3+2] glycosylation of the trisaccharide donor and trehalose acceptor furnished the right hand side pentasaccharide. Regioselective O3 glycosylation of L-rhamnosyl 2,3-diol allowed expedient synthesis of the left hand side tetrasaccharide. The nonasaccharide was assembled in a highly convergent fashion through a [4+5] glycosylation.

Thumbnail image of graphical abstract

Take the strain: First total synthesis of the branched oligosaccharide OSE-1 of Mycobacterium gordonae (strain 990) is reported. An intramolecular aglycon delivery approach was used for constructing the desymmetrized 1,1′-α,α-linked trehalose moiety. Regioselective O3 glycosylation of L-rhamnosyl 2,3-diol allowed expedient synthesis of the left hand side tetrasaccharide. The nonasaccharide was assembled in a highly convergent fashion through a [4+5] glycosylation.

05 Aug 13:19

Selective Protection of Secondary Amines as the N-Phenyltriazenes. Application to Aminoglycoside Antibiotics

by Amr Sonousi and David Crich

TOC Graphic

Organic Letters
DOI: 10.1021/acs.orglett.5b01902
03 Aug 15:36

Simultaneous current generation and ammonia recovery from real urine using nitrogen-purged bioelectrochemical systems

RSC Adv., 2015, 5,70371-70378
DOI: 10.1039/C5RA11556F, Paper
Xiangtong Zhou, Youpeng Qu, Byung Hong Kim, Yue Du, Haiman Wang, Henan Li, Yue Dong, Weihua He, Jia Liu, Yujie Feng
Ammonia could be recovered from human urine through combination of bioelectrochemical systems and nitrogen purging, with concomitant mitigation of ammonia inhibition of anode electroactivity.
The content of this RSS Feed (c) The Royal Society of Chemistry
01 Aug 15:51

Stereospecific Intramolecular Reductive Cross-Electrophile Coupling Reactions for Cyclopropane Synthesis

by Emily J. Tollefson, Lucas W. Erickson and Elizabeth R. Jarvo

TOC Graphic

Journal of the American Chemical Society
DOI: 10.1021/jacs.5b03870
27 Jul 14:45

Chemical Synthesis Elucidates the Immunological Importance of a Pyruvate Modification in the Capsular Polysaccharide of Streptococcus pneumoniae Serotype 4

by Claney L. Pereira, Andreas Geissner, Chakkumkal Anish, Peter H. Seeberger

Abstract

Carbohydrate modifications are believed to strongly affect the immunogenicity of glycans. Capsular polysaccharides (CPS) from bacterial pathogens are frequently equipped with a pyruvate that can be placed across the 4,6-, 3,4-, or 2,3-positions. A trans-2,3-linked pyruvate is present on the CPS of the Gram-positive bacterium Streptococcus pneumoniae serotype 4 (ST4), a pathogen responsible for pneumococcal infections. To assess the immunological importance of this modification within the CPS repeating unit, the first total synthesis of the glycan was carried out. Glycan microarrays containing a series of synthetic antigens demonstrated how antibodies raised against natural ST4 CPS specifically recognize the pyruvate within the context of the tetrasaccharide repeating unit. The pyruvate modification is a key motif for designing minimal synthetic carbohydrate vaccines for ST4.

Thumbnail image of graphical abstract

Unusually Protective. In the search for a glycan epitope for protection against Streptococcus pneumoniae serotype 4, total synthesis of the repeating unit (see structure) enabled the identification of pyruvate as a crucial determinant of immunogenicity. This lays the foundation for the development of a new antibacterial vaccine candidate against Streptococcus pneumoniae serotype 4.

24 Jul 14:08

Regio- and Enantioselective Aza-Diels–Alder Reactions of 3-Vinylindoles: A Concise Synthesis of the Antimalarial Spiroindolone NITD609

by Haifeng Zheng, Xiaohua Liu, Chaoran Xu, Yong Xia, Lili Lin, Xiaoming Feng

Abstract

An asymmetric aza-Diels–Alder reaction of 3-vinylindoles with isatin-derived ketimines has been developed. A series of spiroindolone derivatives were thus obtained in good to excellent yields with excellent enantioselectivity (up to 96 % yield and 99 % ee). Furthermore, the antimalarial compound NITD609 could be obtained in three steps with an overall yield of 40.6 %. Control experiments and operando IR experiments imply a concerted reaction pathway. The regioselectivity and exo selectivity result from π–π interactions between the two indoline rings of the two reactants.

Thumbnail image of graphical abstract

An asymmetric aza-Diels–Alder reaction of 3-vinylindoles with isatin-derived ketimines leads to spiroindolone derivatives with high regio-, diastereo-, and enantioselectivity and also provides facile access to the valuable antimalarial drug NITD609. The stereoselectivity is thought to arise from π–π interactions between the two reactants and the chiral N,N′-dioxide ligand.

22 Jul 14:14

A Small-Molecule Probe for Selective Profiling and Imaging of Monoamine Oxidase B Activities in Models of Parkinson’s Disease

by Lin Li, Cheng-Wu Zhang, Jingyan Ge, Linghui Qian, Bing-Han Chai, Qing Zhu, Jun-Seok Lee, Kah-Leong Lim, Shao Q. Yao
Julia Meyer

Maddy?

Abstract

The design of the first dual-purpose activity-based probe of monoamine oxidase B (MAO-B) is reported. This probe is highly selective towards MAO-B, even at high MAO-A expression levels, and could sensitively report endogenous MAO-B activities by both in situ proteome profiling and live-cell bioimaging. With a built-in imaging module as part of the probe design, the probe was able to accomplish what all previously reported MAO-B imaging probes failed to do thus far: the live-cell imaging of MAO-B activities without encountering diffusion problems.

Thumbnail image of graphical abstract

Seeing is believing: A dual-purpose small-molecule activity-based probe (M2) was developed for imaging the activity of monoamine oxidase B (MAO-B). In situ proteome profiling and live-cell bioimaging of endogenous MAO-B activities from a variety of biological samples, including Parkinson’s disease models, can thus be carried out simultaneously.

22 Jul 14:11

A Priori Estimation of Organic Reaction Yields

by Fateme S. Emami, Amir Vahid, Elizabeth K. Wylie, Sara Szymkuć, Piotr Dittwald, Karol Molga, Bartosz A. Grzybowski

Abstract

A thermodynamically guided calculation of free energies of substrate and product molecules allows for the estimation of the yields of organic reactions. The non-ideality of the system and the solvent effects are taken into account through the activity coefficients calculated at the molecular level by perturbed-chain statistical associating fluid theory (PC-SAFT). The model is iteratively trained using a diverse set of reactions with yields that have been reported previously. This trained model can then estimate a priori the yields of reactions not included in the training set with an accuracy of ca. ±15 %. This ability has the potential to translate into significant economic savings through the selection and then execution of only those reactions that can proceed in good yields.

Thumbnail image of graphical abstract

Getting to grips with yields: A thermodynamically guided calculation of free energies of substrate and product molecules allows the a priori estimation of the yields of organic reactions to be made. The model is first trained on a diverse set of reactions and reaction yields, and can then estimate the yields of other reactions with the accuracy of ±15 %.

07 Jul 17:13

Synthesis of Biologically Active Piperidine Metabolites of Clopidogrel: Determination of Structure and Analyte Development

by Scott A. Shaw, Balu Balasubramanian, Samuel Bonacorsi, Janet Caceres Cortes, Kevin Cao, Bang-Chi Chen, Jun Dai, Carl Decicco, Animesh Goswami, Zhiwei Guo, Ronald Hanson, W. Griffith Humphreys, Patrick Y. S. Lam, Wenying Li, Arvind Mathur, Brad D. Maxwell, Quentin Michaudel, Li Peng, Andrew Pudzianowski, Feng Qiu, Shun Su, Dawn Sun, Adrienne A. Tymiak, Benjamin P. Vokits, Bei Wang, Ruth Wexler, Dauh-Rurng Wu, Yingru Zhang, Rulin Zhao and Phil S. Baran

TOC Graphic

The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.5b00632